I was at the Läderach counter with my son recently, buying chocolate at S$22 for 100 grams. He watched me pay, and I found myself explaining — half to him, half to myself — that this is what work is for. Not to hoard money endlessly, but to be able to enjoy something indulgent once in a while without flinching, and without guilt.
The successful entrepreneur, as far as I can tell, has to hold contradictions that don’t naturally sit well together. Each one sounds like a virtue on its own. Held together, they look more like paradoxes. That’s probably why so few people manage it.
Short-sighted enough to care about immediate profitability. Far-sighted enough not to spend it.
You cannot start a business if you are completely detached from money. At some level, you have to be driven by it. You have to notice a gap and feel enough urgency to do something about it.
For me, that was noticing that a specific niche of fitness equipment was hard to buy in Singapore. By around 2010, CrossFit was already taking root here, but the ecosystem around that kind of equipment still felt fragmented. There was demand, but the supply side hadn’t matured.
That’s the short-sighted part. You have to care about the first dollar in — whether people will actually pay.
The harder part comes after. You have to be far-sighted enough not to enrich yourself too early. You watch the bank account climb and resist the urge to consume the result. You keep putting money back into the machine — inventory, supplier depth, the subsequent business via horizontal or vertical expansion, then some. The process took me more than fifteen years, and at many points I could have taken money out. At many points I could have rewarded myself earlier.
That’s where most people break. They have one good business, one good year, maybe two, and they assume the trajectory is now permanent. They buy the luxury car. They upgrade the lifestyle. They stop compounding at exactly the point compounding would have started to matter. They confuse early validation for arrival.
The irony is that to start, you need to care enough about money to chase it. But to build something lasting, you need to become detached enough from it not to spend it.
Smart enough to qualify for the top track. Street-smart enough to walk away from it.
In Singapore, the path for strong students is very clearly marked. If you were in a special stream, the expected move after O-levels was JC, then a local university with a scholarship from a ministry or an MNC, then a bonded career that is fast-tracked.
I went to polytechnic in 2004 instead.
At the time, this looked like some combination of stupidity and bravery, mostly the former. The tilt toward the JC route wasn’t imagined. In 2008, of every 100 students in a cohort, 25 entered the three subsidised local universities — 19 through the JC route and only 6 through polytechnic. The university route then was structurally more oriented toward JC.
What I only realised later was that polytechnic suited me far better than the conventional path would have. The curriculum was directly aligned with what I actually wanted to learn, which was business. It was also, frankly, easier academically than JC. That gave me more room to explore, more time to pursue other interests, and less of the exhaustion that comes from grinding through a prestigious path by default.
Then came the second-order effect. Many of my JC peers arrived at university already burnt out. They had told themselves JC was the sacrifice and university would be the reward, so by the time they got there they wanted to play. They treated university as the last checkpoint before adulthood, and some of them took their studies too lightly. I arrived fresher, with a better relationship with studying, and could push hard when it actually mattered.
The same logic showed up later whenever scholarships were dangled as the obvious next move. In OCS, the army tried to sell me one — local or overseas, bonded to the organisation afterwards. On paper the pitch is always attractive: prestige, security, a defined path, a sense that you’ve been chosen. But street-smartness begins where the official pitch ends. You count the years. You see the cost of bonds, of lost optionality, of a life that looks good on paper but is already spoken for. The pitch always skips the cost side, and that’s exactly where the asymmetry lives.
Sometimes the smartest move is not to take the path designed for smart people.
Brave enough to leap. Discerning enough not to be stupid.
The line between bravery and stupidity is thin, and it is only visible in retrospect. Choosing polytechnic over JC could have turned out stupid. Starting Movement First could have turned out stupid. Many of the expansion decisions I’ve made along the way looked unnecessary, reckless, or overconfident until enough time had passed for people to relabel them as bold. That is one of the cruellest things about entrepreneurship: the judgement is always retrospective.
Ark Bloc was one of those bets. We took on a 15,000 sqft space that was effectively a sheltered shed — no walls, no fit-out — and spent a significant sum retrofitting it. The math only worked if the lease played out a very specific way: signed in Feb/March with two months rent-free, opened in May, with an initial term only running to 2025. For the economics to hold, we needed SLA to renew the master lease for another two or three years and not five, so that the landlord would not be able to find a replacement tenant easily and we would have leverage to negotiate a modest rent increase at renewal. If revenue growth disappointed, if SLA declined to renew the master lease, or if the lease got extended too long at the wrong rent, the capital we had sunk in would be gone. Objectively, for the win probability we were underwriting, it was probably stupid.
The thesis played out. We had designed Ark Bloc around bouldering, strongman and functional fitness, but by luck more than foresight, the layout and stations mapped almost perfectly onto Hyrox, which boomed from 2022 onwards. The lease got renewed in 2023. We’re still waiting to see whether it gets renewed again at the end of this year. The bet hasn’t fully resolved.
That’s the honest shape of these decisions. At the time of the leap, I could not have told you with confidence which side of the line we were on. I could only tell you that the downside was survivable and the thesis rested on something real — actual demand for bouldering and functional fitness space, an actual scarcity of 15,000 sqft shells in the right catchments. Those two conditions are what separate a brave bet from a stupid one, at least in my experience. The people who stay on the brave side usually insist on both. The people who end up on the stupid side usually skip one or the other.
Where it breaks
I’ve seen two failure modes more often than any others, and they are the same paradox running in opposite directions.
One group is too far-sighted. They chase a grand vision without doing the unglamorous work of figuring out who their first twenty paying customers are. They build a beautiful product for a market they haven’t properly spoken to. They confuse ambition with traction.
The other group is too short-sighted. They do get traction. They do make money. But they mistake the first upward slope for the whole curve. They cash out too early, upgrade their lives quickly, and stop reinvesting at exactly the moment they should be doubling down.
One dreams without grounding. The other earns without discipline. Both fail on the same axis, just from opposite ends.
When my son is older, I’ll probably tell him some version of this. Work hard enough that you can buy the chocolate without flinching. But don’t get so attached to the chocolate that you stop compounding the thing that bought it.
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