Inside the Mind of the Structurer - Old Weapons for the New War

Mars Attacks – The Trashy Movie that Explains Everything

I must have watched Mars Attacks! more than ten times as a kid.

It played on television constantly—one of those movies that networks repeated on slow afternoons. I never changed the channel. I was very young. I did not know who Tim Burton was, or that the movie was considered campy, or that adults thought it was trash.

I just knew it had Martians. It was the first time I had ever seen Martians on screen. That was enough for me.

The plot is simple. Aliens invade Earth. The military throws everything it has at them—fighter jets, tanks, nuclear warheads. The full arsenal of human technology.

Nothing works.

The aliens shrug off every weapon. The most advanced technology on the planet is useless.

Then, by accident, a grandmother’s music starts playing. Slim Whitman. An obscure country yodeler from the 1950s—the kind of music nobody under seventy would choose to listen to. It comes through the speakers.

The aliens’ heads explode.

As a kid, I just thought it was hilarious. The grandma saves the world. The annoying music kills the aliens. The Pentagon’s billion-dollar weapons are useless and this ridiculous thing nobody took seriously turns out to be the answer.

I did not realize it then, but that scene taught me something I have carried for thirty years.

The most obvious solution is not always the solution.

—

Many years later—last year, in fact—I was walking through the cold street of Seoul, preparing a speech.

I had been invited to deliver the closing lecture for a derivatives course at ESSEC Business School. The students were MBA candidates. They had spent months learning option pricing and binomial trees. My job was to talk about how structurers think.

And as I walked, I kept circling around a frustration that had been building for a decade.

First-principles thinking has been glorified.

The Religion of First Principles

First-principles thinking has been glorified.

Elon Musk made it famous. The idea is elegant: strip any problem to its most fundamental truths. Ignore convention. Rebuild from scratch. What is a rocket made of? Aluminum, titanium, copper. What do those cost? Two percent of the typical price. Therefore, you can build rockets ninety-eight percent cheaper.

It is brilliant. And it has become, in business schools and boardrooms and conference stages around the world, the gold standard of intelligent reasoning.

Meanwhile, the way I think—the way every structurer I know thinks—has been treated as something lesser. Reasoning by analogy. By comparison. By looking at what already exists and adapting it. This kind of thinking is dismissed as unoriginal. Mimetic. The lazy cousin of real thought.

Here is what I have never admitted publicly until now: I believed that story for ten years.

When I turned thirty, I wanted to reinvent myself. I discovered first-principles reasoning and fell in love with it. I tried to make it work in my world. And for a decade, I felt inadequate—because my instinct was always to compare, to adapt, to borrow. I actually hated my derivatives skillset. It felt old. Uncool. The opposite of the Silicon Valley way.

But on that walk through Singapore, something shifted. I stopped fighting my own mind.

And I asked a different question.

What if the old way is not inferior? What if it is different—and in many situations, better?

What if the Slim Whitman record is the answer?

•  •  •

Why the Grand Solution Usually Fails

 Here is what Elon Musk does not talk about.

First-principles thinking assumes a blank canvas. It assumes you can strip the world to its atoms and start from zero. For a man with billions of dollars and the ability to hire any engineer alive, this works.

Most of us do not have a blank canvas.

Most of us operate under constraints. Limited capital. Regulatory boundaries. Institutional politics. Imperfect information. And real human beings who do not behave the way models predict.

I have spent nearly twenty years in banking. And in banking, first-principles thinking runs into a wall that physics never encounters.

People.

First principles assumes the world is like physics—if you find the fundamental truth and build from it, the solution will work. But physics does not have emotions. Physics does not have career incentives. Physics does not have a risk committee that says no because the last deal like this blew up in 2008 and nobody wants to approve the next one.

I have watched the grandest solutions fail. Not because they were wrong. Because they did not connect.

Sometimes the structurer could not explain the product to the people who held power. Sometimes the solution was technically brilliant but ignored the client’s psychology. And sometimes the world as it is simply defeated the world as it should be. The people in the room looked at the elegant answer and said no. Come back with something we understand.

Banks are organized with Byzantine complexity. Three lines of defense. Compliance. Legal review. Risk committees. Credit approval. This is not dysfunction. It is designed for control. But it means every idea must navigate a maze of stakeholders, each in their own silo, each with their own context, their own incentives, their own fears.

First-principles thinking says: strip all that away. Find the truth.

But you cannot strip it away. It is the water you swim in.

I have used first-principles thinking many times. Almost every time, it sounds brilliant on Day One. The presentation is clean. The logic is airtight. People nod.

Then comes Day Two. People start talking to other people. The silos engage. Context floods in. And the elegant solution stalls.

The worst outcome of first-principles thinking is not a wrong answer. It is a deadlock. A beautiful idea that nobody can execute because it was designed for a frictionless world, and the world has friction everywhere.

•  •  •

Analogy Is Not Copying

When someone tells me that analogy is just copying, I push back.

Analogy is not copying. Analogy is thinking through what you can replicate—from existing instruments, existing structures, existing solutions in adjacent domains—that is good enough to satisfy all the constraints and reach a deal. The key phrase is “good enough.” Not perfect. Not optimal. Good enough to move.

In a world where you are working with irrational people, with regulators who have their own agenda, with clients who fear what they do not understand, with committees that are designed to say no—a different kind of thinking is necessary. Not reasoning from atoms. Reasoning from constraints. Not building from scratch. Building from what exists. Not pursuing the theoretically perfect. Pursuing the practically achievable.

And this kind of thinking—this disciplined analogy—has a powerful advantage that first-principles thinking does not: it is persuasive. When you present a solution that is built from familiar components—instruments the risk committee already understands, documentation the legal team already approves, structures the regulator has already seen—the path to “yes” is shorter. People can imagine it. They can see how it works because they have seen the parts before, even if the combination is new. Analogy makes the unfamiliar feel familiar. First principles makes the familiar feel alien.

That is not a deficiency. That is a superpower.

•  •  •

The Philosopher Behind the Contrarian

 A biography of Peter Thiel introduced me to the philosopher who changed how I think about all of this.

His name is René Girard.

Girard spent his career at Stanford, and his central idea is disarmingly simple: human beings do not know what to desire on their own. We learn what to want by watching what others want. Our desires are not original. They are borrowed.

He called this mimetic desire. Our tendency to copy.

Thiel built his entire investment philosophy on Girard: escape the mimetic trap. Be contrarian. Find the thing nobody else wants and pursue that.

I agree with Thiel—in the long run. You need original positioning eventually.

But in the short run—in the daily work of getting things done in organizations full of real people—deliberate imitation is not weakness. It is the most powerful tool you have.

Think about what a structurer actually does. The structurer does not invent new financial physics. The structurer looks at existing instruments and asks: can I adapt this? Can I recombine it? Can I take something built for one purpose and repurpose it for another?

The first currency swap in history was not invented from first principles. It was assembled from a dollar bond and a currency exchange—two existing things, combined in a way nobody had tried before. The credit default swap was not conjured from atoms. It was insurance concepts applied to credit risk using derivatives documentation.

Analogy is not copying. Analogy is thinking through what you can replicate that is good enough to satisfy all the constraints and reach a deal.

And when you show a risk committee something analogous to something they already understand, something clicks. They can imagine it. They can see themselves approving it. You have reduced the distance between the new and the familiar.

That is not inferior reasoning. That is how things actually get done.

 What a Structurer Actually Does

 If you have never heard the word “structurer,” you are not alone.

Here is how I explain my job: I am a chef.

I love cooking. I cook risotto, and when I look at a handful of rice, I see endless combinations. Different broths. Different proteins. Different aromatics. All producing different results from the same basic grain. A good chef knows the ingredients deeply, knows how they interact, and knows the palate of the person at the table.

A structurer does the same thing in financial markets. The ingredients are basic instruments—bonds, forwards, options, swaps. Each one is simple on its own. But combined correctly, they produce payoffs that no single instrument possesses. Tailored to a specific client. Within specific constraints.

I entered this profession in 2008, at the worst possible moment. The global financial crisis had just detonated. Derivatives had become the D-word—the demon word. Nobody wanted to touch anything with “structured” in its name.

Most people saw catastrophe. I saw opportunity. If derivatives were misunderstood, then someone needed to help people understand them properly. I started one of the first courses on derivatives at a prestigious Philippine university. And I began pondering the deeper reality of what derivatives actually are.

Not the instruments. The way of thinking that produces them.

Because the good structurer is not the one who knows the most formulas. The good structurer is the one who knows the ingredients deeply, understands how they interact, and—above all—satisfies the palate of whoever they are trying to serve.

•  •  •

The Outsider’s Mindset

Eight years ago, I moved to Singapore.

In global banking, the market you come from is a signal. People read it instantly. If you come from London or New York, you carry credibility before you open your mouth. If you come from Manila, you carry something else.

I was an outsider. Again.

You cannot first-principles your way into belonging. There is no fundamental truth you can derive that tells you how to navigate a new culture, a new hierarchy, a new set of unwritten rules.

So I did what I have always done. I watched. I compared. I adapted. I went where Singaporeans go—hawker centers, churches, workplaces—and tried to understand rather than be high and mighty about it. I used the same thinking that had built my career: analogy, observation, disciplined borrowing.

I looked at the people who had navigated what I was trying to navigate. I studied what they did. I adapted it for my situation.

And over eight years, from that constrained starting point, I rose to lead structuring across Asia-Pacific. That is rare for someone from the Philippines. The heads of structuring typically come from London, New York, Hong Kong. I came from a market that most people in the industry cannot find on a map.

During those same years, I lost thirty kilograms.

Not through some revolutionary insight. Through the structurer’s mindset. I read books on diet, exercise, and sleep. I compared approaches. I decomposed the problem into parts I could control. I identified compromises I could sustain—because a diet you cannot maintain is like a hedge you cannot hold. I tried to love what I hated by understanding what made it painful and reducing the friction, one piece at a time.

Same method. Different domain.

The seven mental models I will share in this book are not abstract theories I encountered in a classroom. They are instincts I developed through hard-won, battle-tested experience—in structuring, in career, in health, in the messy business of building a life from constrained materials.

•  •  •

Seven Mental Models for Thinking in Constraints

 This series maps seven ways of thinking.

Decomposition — every complex problem is a combination of simple problems. Break it apart first.

Combination — when you put the parts back together, something new emerges. Something no individual part possesses.

Multidisciplinary Thinking — the person with one mental model distorts every problem to fit it. Carry many.

Synthetic Replication — when the thing you need does not exist, build it from what does. Then be honest about the gap.

Compromise Design — the gap between what people fear and what is actually dangerous is where you build.

Exception Thinking — models describe the world as it should be. You live in the world as it is. Know exactly where the model breaks.

The Hedging Argument — worry about risk first. Return will follow.

Together, these seven models produce three capabilities that matter more now than ever: genuine creativity, social connectivity, and critical thinking under ambiguity.

These are the things that make you human.

They are also the things that no machine does well.

•  •  •

Why Am I Writing This

 I am writing this during my daughter’s PSLE year and my son is getting interested in many things.

If you live in Singapore, you know what that means. The national exam. The tuition culture. The pressure on ten-year-olds to study hard, master the syllabus, and produce the right answer under time pressure.

I watch my daughter prepare, and I think about what she is actually being trained to do. Analyze problems. Apply frameworks. Optimize within defined rules.

And then I think about what artificial intelligence does best.

Analyze problems. Apply frameworks. Optimize within defined rules.

We are drilling into our children the exact skills that machines are learning to do better than any of us. The race is already over. The machines won.

So the question that keeps me up at night is not how to help my children compete harder. It is how to equip them with the capabilities that machines do not possess.

The ability to reason by analogy. To find connections between things that have never been connected. To navigate the fears and incentives of real human beings. To build from constraints instead of from abstractions. To know where the model breaks before reality shows you.

That is what this book is.

It is not a finance book. Finance is the proving ground. The lessons are universal.

It is a book about a way of thinking that was forged under pressure, in trading rooms and treasury desks, by people who could not afford to reason from blank canvases. An old way of thinking. Not fashionable. Not celebrated. But tested—across markets, across crises, across the messy, imperfect, constrained reality of professional life.

I want my children to see constraints as friends. Because constraints do not limit creativity. They focus it. They demand that every move count. And they produce solutions that are more resilient, more grounded, and more human than anything a blank canvas ever will.