Hey everyone,

So the benchmark Straits Times Index crossed 5,000 for a second time this week, having recovered from falling to below 4,800 in the immediate aftermath of the Iran War.

Banks again, and in particular DBS, did the heavy lifting. Shares of Singapore’s biggest bank are up over 10% in 2026 and it closed above $62 for the first time ever.

The seemingly-perennial question in Singapore: Is it a good time to buy bank stocks? That very much depends on the entry (dividend) yield you’re happy with and being conscious of the differences between the three.

However, at the end of the day, it’s worth sizing single-line security (i.e. single stock) positions more responsibly. From a risk management perspective, no one stock should make up more than 5% of your overall investment portfolio but you could always stretch that to 10% if you feel strongly about it.

Either way, just be aware that outsized positioning on single stocks can really impact your portfolio. The good times might be rolling now but when we’re building (and then focused on preserving) wealth, position sizing becomes that much more critical.

A few things I wanted to cover this week:

Why five of Singapore's biggest blue chips have been quietly buying back their own shares, and how you can think about it.

Then, how do you actually rebalance an ETF portfolio without overcomplicating it? And finally, my latest YouTube video on how much you really need to retire in Singapore, with the honest maths broken down.

Let's get into it.

How do you actually rebalance an ETF portfolio? It's one of those things that sounds more complicated than it is.

Rebalancing just means bringing your portfolio back to its target allocation. Say your target is 60% stocks, 40% bonds. Over time, if stocks have a good run, that mix might drift to 66% stocks and 34% bonds.

To rebalance, you trim the 6% that's grown beyond target and put it into bonds, bringing you back to 60/40. That's the whole idea. Sell a bit of what's run up, top up what's lagged, return to your targets.

You don't need to do this often. Once every 6 months or 12 months is plenty. Checking and tinkering more frequently than that tends to do more harm than good.

The thing that actually makes rebalancing easy is keeping your portfolio simple in the first place. If your core is one global equity ETF and one global bond ETF (or your CPF as a de facto bond allocation), rebalancing is a two-minute job. If you're holding fifteen different positions, you make the task much harder than it needs to be. A basic 60/40 can genuinely be just two ETFs.

One point that trips people up is that there’s a difference between rebalancing within a fund and rebalancing across your portfolio. If you hold a broad global ETF like the Vanguard FTSE-All World UCITS ETF (VWRA), the ETF itself handles the country and company weightings for you, reweighting periodically as markets move, either twice a year or four times a year depending on the index provider.

You don't touch that because your job is only to rebalance between your own buckets, so stocks versus bonds versus any small allocation to alternatives like gold or REITs.

If you want a small "alternatives" sleeve, gold or REITs work as a diversifier, but keep it to no more than 10% to 15% of the core portfolio. The bulk should stay in your stocks and bonds/CPF.

That's really it. Set your target, check in once or twice a year, and resist the urge to fiddle in between.

If you’re a decision maker at your company, you need to be on the bleeding edge of, well, everything. But before you go signing up for seminars, conferences, lunch ‘n learns, and all that jazz, just know there’s a far better (and simpler) way: Subscribing to The Deep View.

This daily newsletter condenses everything you need to know about the latest and greatest AI developments into a 5-minute read. Squeeze it into your morning coffee break and before you know it, you’ll be an expert too.

Subscribe right here. It’s totally free, wildly informative, and trusted by 600,000+ readers at Google, Meta, Microsoft, and beyond.

You've probably seen the retirement numbers thrown around online. One million. Three million. Five million. Sometimes even $10 million.

Most of those numbers are either scaremongering or imported straight from US calculators that completely ignore CPF. So I sat down and did the honest maths for Singapore.

In my latest video, I break it down properly. Three retirement lifestyle tiers with real monthly figures. What CPF LIFE actually covers (the part most calculators get wrong).

And exactly how much you'd need to invest each month to hit your number, based on reaching the Enhanced Retirement Sum (ERS) in your CPF RA at 55.

The numbers might surprise you. A comfortable retirement in Singapore needs a lot less than the doom posts suggest. But there's a catch most people don't see coming.

If you're in your 40s, approaching retirement, and want help thinking through your own portfolio, I'm putting together an Investing for 45+ workshop.

Join the waitlist here and I'll be in touch when it opens.

Something's been happening on the SGX over the last few months that I don't think is getting enough attention.

Singapore companies have spent over S$900 million buying back their own shares in just the first four months of 2026. Five names account for the bulk of it, and they're some of the biggest companies on the market.

A quick refresher on what a buyback actually is. A company uses its own cash to repurchase its own shares, which reduces the number outstanding. Fewer shares means each remaining one represents a slightly bigger claim on the business. Alongside dividends, it's one of the two main ways a company returns profits to shareholders, and it can be a signal that management thinks the stock is undervalued.

Here's the top five, smallest to largest:

So what do you actually do with this?

Not much on its own, honestly. Buybacks get talked about as a signal that a stock is cheap, and sometimes that's true. But companies are also notoriously bad at timing their own buybacks. So I wouldn't treat any single one as a reason to rush out and buy.

What's more interesting is that all five are constituents of the Straits Times Index (STI), and combined they make up around 40% of the STI. So if the trend interests you and you want exposure to these names, you don't need to pick between them. A simple STI ETF gives you a slice of all five in one go.

On SGX, that's the SPDR STI ETF (ES3) or the Amova STI ETF (G3B). Both pay dividends twice a year and yield around 3.5%. If you'd rather have the dividends automatically reinvested, the Amova STI ETF also comes in an Accumulating share class under the ticker GAB.

If there's a topic you'd like me to break down in a future edition, hit reply and let me know. The best ideas in this newsletter come from your replies.

Until next week,

— Tim

1. Investing Made Simple: A self-paced course that walks you through building a proper investment portfolio from scratch. ETFs, allocation, brokers, and the mindset to stay consistent. Everything you need to start and keep going. Join here.

2. Miles Made Simple: A strategy guide for earning and redeeming KrisFlyer miles the right way. If you're flying out of Singapore and not optimising your credit card spend, you're leaving a lot on the table. Get the guide here.

3. Got a question? Submit it here and I might answer it in a future edition.