Legacy - Uncle Huat's Sharing

🧱 Series: Bloodlines and Bottom Lines – The Untold Stories of Family Business

Have you ever seen two aunties fighting over who gets their mother’s Nasi Lemak recipe? Now imagine that same dynamic… but it involves property, millions of dollars, and 20 years of blood, sweat, and unspoken expectations. (p/s: if you are in Singapore, you will see there are many hawker families that split because of the recipes and this CNA’s series documented it very well – food feuds)

Welcome to family business.

In Part 1, we met the Tan brothers—five siblings who built something special together, only to see it unravel when unspoken promises clashed with legal reality. But the Tan story? It’s not an outlier. It’s a pattern.

So why does this keep happening?

Let’s peel back the curtain on the quiet chaos behind many family-run businesses in Singapore—and more importantly, what you can do before it’s too late.

🧨 Reason 1: “We’re family. No need to write anything down.”

Sound familiar?

It’s the most common refrain I hear when advising family enterprises. There’s this deep cultural reflex—especially in Asian households—that says formalising agreements means you don’t trust each other.

But trust isn’t about handshakes. Trust is about clarity.

Let’s say Ah Seng promises his younger sister Mei Li that she’ll get 20% of the business “next time.” Everyone nods. Fast forward 15 years. “Next time” never came. And suddenly, Mei Li is scrolling through ACRA with a glass of wine and a rising sense of betrayal.

If it’s not written down, it never happened. Period.

💥 Reason 2: Mixing roles and relationships

In theory: your eldest son handles the books, your second-born runs operations, and your daughter helps “when she’s free.”

In reality? You’ve got overlapping responsibilities, zero accountability, and someone’s spouse complaining over dinner about “carrying the whole business.”

Here’s the deal—just because someone is family doesn’t mean they’re qualified. And just because someone is qualified doesn’t mean they want to take over.

Clear roles, job descriptions, and performance reviews aren’t just for MNCs. They protect relationships. They prevent sibling rivalries from turning into full-blown shareholder wars.

🪤 Reason 3: The Next Gen isn’t ready. Or worse, they don’t want it.

You’ve probably heard this saying:

First generation builds it. Second generation grows it. Third generation blows it.

Harsh, but there’s truth in it.

Many founders work 16-hour days to build something meaningful… but forget to build foundations for succession. So when it’s time to pass the baton, they realise no one’s been trained, no one wants the stress, or worse—everyone wants control, but no one wants responsibility.

If you’ve never had a proper family business meeting about succession, expectations, and vision… it’s not too late. But you’ve got to start before it becomes a fight over your hospital bed.

📉 Reason 4: Money makes things weird.

Let’s be real. We don’t like talking about money in most Asian families. It’s “not nice,” “disrespectful,” or “later then discuss.”

But money is the bloodstream of a business. If your brothers don’t know who actually owns the shoplot, or your kids think “everything is 50/50” because you love them equally… you’re sitting on a landmine.

Transparent communication about ownership, dividends, salary, and reinvestment isn’t greedy—it’s governance. And it keeps Christmas dinner drama-free.

📈 Reason 5: There’s no plan… just vibes.

Far too many family businesses run on vibes, not vision. Everyone’s “just trying their best.” But there’s no roadmap. No strategy. No emergency plan if dad falls sick or the market tanks.

Sound familiar?

Without clarity, emotions fill the void. And once egos enter the chat, it’s very hard to walk it back.

So, What Can You Do?

Start talking. Set up regular, structured family business meetings. Not every dinner needs to turn into a boardroom… but some should.
Get it in writing. Use shareholder agreements, employment contracts, and wills. It’s not a lack of trust—it’s a sign of respect.
Bring in help. Whether it’s a family business coach, a lawyer, or your accountant—external professionals can ask the awkward questions and create safe boundaries.
Respect the boundary between family and business. One is built on love. The other runs on structure.

🎯 Quick Self-Check: Are You Running a Business or a legacy Time Bomb?

☐ Do you have clear written agreements about ownership and roles?
☐ Have you had an open conversation about succession?
☐ Are family members being paid fairly and transparently?
☐ Do you have a mechanism to resolve disputes (that’s not “see you in court”)?
☐ Is everyone clear on your vision for the future?

When Family and Business Collide – bloodlines or bottom-lines?

Have you ever sat down, kopi in hand, and thought, “Wah, family sure got drama—but at least business is different”

Yeah… About that.. hold on to your seat, although this story is not as widely spread like the recent CDL saga, but there are plenty of learning from this drama.

I had coffee recently with a friend—let’s call him Gerald—who’s a lawyer and he shared with me a legal tangle that sounds like an episode of “Succession,” except it’s set in MacPherson, not Manhattan. (You can google the case most probably you will find it)

His story isn’t rare. In fact, it echoes a real case I came across not long ago. And it’s one of those stories that makes you pause and think: “Can blood and business really mix?”

Business is thicker than blood?

Yea.. of course it is an ai generated picture – can’t find the heart to use any other family’s picture for this article.

Let me tell you about the Tan brothers (Not their real name, of course).

You know the type.. Five brothers, grew up working shoulder to shoulder in their dad’s construction business. From the dusty sites of Toa Payoh to the steel frames of Upper Thomson, they were inseparable. They hustled, saved, and eventually pooled resources to buy over a property company—let’s call it Holdings One Pte Ltd (again, not the real name).

Now, here’s where the plot thickens.

Initially, only the two eldest – Ah Fong (Brother 1) and Ah Kheng (Brother 2) – were listed as shareholders. “For simplicity,” they said. “We’re all in this together,” they promised. And everyone nodded because, well, they’re family. Trust is like pandan waffles – best enjoyed warm, with no surprises.

Fast forward 20 years. Properties bought, redeveloped, sold. Money flowed in. Some was reinvested, some (allegedly) loaned in, and some mortgaged. But when the younger brothers Ah Tong (Brother 3), Ah Kang (Brother 4), and Ah Pang (Brother 5) – decided to check the company’s registrar one day in 2019 (imagine that feeling, like finding out your Kaya Toast have no Kaya), they saw their names… and they weren’t there!

Instead, shares they thought were theirs had been transferred back to Ah Fong. Quietly. Without a whisper.

“Maybe it’s a mistake?” one of them said.

It wasn’t.

What followed was a family implosion. Courtrooms instead of CNY reunions. Lawyers instead of love. Claims of trust arrangements from the 90s, a “Company Resolution” they all signed in 2012, and share transfers that apparently came with no payments.

The older brothers said it was a sale. The younger ones said it was a gift based on long-standing trust and shared effort.

Who’s right?

The High Court eventually ruled in favor of the younger brothers. Turns out, those family agreements—though informal, even a little messy—can still hold water when backed by years of consistent behavior, financial contribution, and a bit of documentation. But by then, the damage was done.

No more family dinners. No more “I got your back.” Just silence. The kind that echoes even louder in a small island like ours.

So what do we take away from this?

Look, I’ve been in corporate finance for over 15 years. I’ve helped founders exit for millions and guided families navigating sticky shareholder exits. But nothing—and I mean nothing—is more volatile than a business built on assumed trust with zero structure.

Because here’s the hard truth: feelings fade. Memories get fuzzy. But paper—paper doesn’t forget (plus now digitally it is uploaded and saved somewhere).

If you’re building a business with family, here are three lessons that you must not forget:

Put it in writing. Trust is great. But contracts preserve trust. Don’t rely on verbal agreements from the ’90s when today’s assets are worth millions.
Separate roles from relationships. Your eldest brother may have raised you, but that doesn’t make him your CFO if he is not financially trained. Know and define who’s wearing what hat—and the responsibilities and accountabilities that come with it.
Review and refresh. Businesses evolve. So should your agreements. What made sense in 2012 may not work in 2025. Update your shareholder structure, especially when new projects or people come in.

Today, there’s a growing trend of family offices and succession planning in Singapore – especially with so many SMEs hitting the second or third generation. That’s a good thing. But plans only work when they’re followed.

There is a chinese saying “富不过三代” (fù bù guò sān dài), meaning “wealth doesn’t last three generations”, but with proper legacy and wealth planning, it could last more than three generations and the legacy last for the many generations to come.

So next time when you are hanging out with your family-business-partner, ask: “Eh, bro… we really clear on this or not? Let’s get the paper work done and sign it.”

Because if not, you might find your next family meeting happening… in court.

What do you think? Have you had to navigate business with your family before? Share your experience—anonymously or not— by dropping me an email (TalkTo@unclehuat.com). Let’s start the conversation.

When Love Meets Liability: Why Family Businesses Fail (and How to Stop It)