The Rich Cab Driver

On a Friday night in March 2018, my wife and I were in a cab heading home from IKEA — a date night, because that’s the kind of exciting couple we are kakakakaka — and the driver started talking business.

Not small talk.

Advice.

Unprompted, structured, and delivered with the confidence of a man who had clearly given this lecture before:

Don’t waste your prime years climbing toward a big salary — they’ll work you past its worth and you’ll come home dead anyway. Build something you own while you still have the energy. Keep cashflow tight in the early years, because most businesses die in the first two and your only job is to not die with them. He talked about funding — he’d once been backed with half a million dollars to start his own venture. He explained bank factoring to us, in a cab, with examples.

It was a good lecture.

And here’s the honest part: I’ve forgotten most of it. I had to dig up something I wrote the following year to reconstruct the list above. The factoring explanation, the funding war story, the survival statistics — all of it slid off me within months.

One thing stayed.

Seven years later I can still hear it:

“All four of my children are business owners. Now what I do is teach my grandchildren.”

The portfolio he was actually driving home to

Sit with what that sentence means.

A man at the tail end of his working life, driving a cab on a Friday night, whose actual life output was four children who all build and own things — and who had moved on to the next generation, deliberately, as a project. He wasn’t reminiscing. He used the word teach. It was present tense.

It was his current occupation; the cab was just the shift.

Most men his age, if you ask what they built, point to a career. He pointed to people. The advice he gave us about factoring was secondhand knowledge. The thing about the grandchildren was a balance sheet.

Why that line, and not the others

For years I thought the lesson of that cab ride was the advice. It took me a long time to see that the real data was in the filtering — in what my memory kept and what it threw away.

Memory is not a recorder.

It’s a sieve, and the mesh is shaped like whatever you’re actually seeking — including the things you’re seeking before you can name them. I forgot the funding mechanics because I didn’t need a stranger’s funding story. I kept the grandchildren line because that was the question my life was quietly asking.

And the timing tells me why.

That March, I was at a crossroads between businesses — one chapter closing, the next not yet chosen. Sitting in the back of that cab, the live question underneath all my spreadsheets was not what do I build next but what is any of it for. And a stranger answered the second question while I was still pretending to ask the first: the building is the curriculum.

The children are the work.

So here’s a diagnostic you can run on yourself, free of charge: think of advice you received years ago — a mentor, a book, a stranger.

Don’t evaluate what they said. Look at which line survived. The surviving line is rarely the most useful thing they told you. It’s the most accurate reflection of what you were listening for. Your memory has already told you what you value. Most people never check the receipt.

What I’m doing with it

That driver’s grandchildren probably don’t know that their grandfather lectured two strangers about them in a cab in Tampines. That’s the nature of transmission — it mostly happens in vehicles, at bedsides, across dinner tables, unrecorded, while everyone thinks the real work is happening elsewhere.

These days I tell my own children stories in the car. I think about that driver more than I expected to. He gave me an hour of business advice, and the only thing I kept was the sight of a man who had already moved his wealth into people — and was still compounding it, one grandchild at a time, between fares.

I forgot his tips.

I’m trying to become his evidence.

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