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.