Multibaggers and Skeletons: Who We Think We Are

There is a person in almost every social gathering who won't pick up a hammer to hang a painting.

They know this about themselves. They've learned it the slow way, through stripped screws, uneven frames, the particular frustration of a job that looked simple and wasn't. They've made peace with it. They call someone.

The same person will open a self-directed brokerage account without hesitation.

It is about who you might get to be.

Not a better investor, necessarily. A different person. More decisive. More skilled. More right. Someone whose judgment the market has validated. Someone with a story worth telling at the next gathering rather than listening to someone else's.

The investing account becomes a place where that version of yourself might finally exist. A place where the sense of agency that can feel elusive elsewhere might finally be exercised.

Investing is uniquely seductive for this purpose.

The language sounds like expertise before any outcome has arrived. Thesis. Conviction. Position sizing. The feedback is delayed long enough to sustain the illusion. A crooked nail is visible immediately. A bad trade thesis can look like patience for months.

I had a client I had worked with longer than almost anyone else.

The relationship had been built over years, through market cycles and life events, through the kind of accumulated trust that only comes from having been there for both.

At some point he opened a self-directed account.

He mentioned it during a review. Casually. The way you mention something you're slightly proud of but don't want to oversell.

A few months later he mentioned it again. This time with more enthusiasm. He had found something, a position that had moved significantly. A multibagger. He walked me through the thesis, the timing, the return.

I listened.

The dangerous part wasn't that the first position went up. It was that it went up enough to become evidence of a new identity. He was, as a good outcome can make you feel, certain he understood something the market had only recently recognized.

Over the next several reviews he brought it up again. The account was growing, and the position continued to validate his belief in his own judgment.

Then he stopped mentioning it.

Not abruptly. Gradually. The way a topic fades when the story it was telling has changed.

I noticed the silence before I said anything about it. A few reviews passed. I waited, the way you wait when you sense something has shifted and you want the other person to find their way to it.

Eventually I asked.

Could I see the statement?

He showed me without hesitation. The multibagger was still there, smaller now, but present. Around it, a series of other positions. Each one a thesis. Each one, by the numbers on the page, a loss.

The account overall was underwater.

He didn't need me to say anything. The statement said it.

What he said, after a moment, was this:

I think I got lucky with that first one. I didn't have the discipline to replicate it. I kept thinking I understood something I probably didn't.

I didn't say I told you so.

Not because I was being polite. Because that sentence would have ended something that had taken years to build. The relationship wasn't built on me being right. It was built on me being present through enough cycles, enough decisions, enough moments when the outcome didn't match the intention, that he could say what he said without it costing him something.

The multibagger story is not necessarily dishonesty.

Every room has someone telling one. What the room never hears is the other story. The position held too long after the thesis had clearly broken. The account that grew quietly smaller while the winning trade was being discussed elsewhere.

Those stories exist behind the winning versions we rarely hear.

They just don't get told.

And told often enough, to enough people, in enough rooms, the edited story starts to replace the unedited one. The problem isn't simply that luck can masquerade as skill. It is that luck can imitate skill for long enough to make the distinction almost impossible to see from inside the story.

We don't compartmentalize as well as we think. The person who procrastinates in life procrastinates on the sell decision. The person who needs to prove something elsewhere brings that need into every trade they make.

The portfolio is not a separate rational domain. It is an extension of the person making the decisions. All of them. Including the parts that don't get mentioned at the review.

The skeletons don't disappear.

They wait. In accounts that stop being mentioned. In positions that quietly become smaller. In the gap between the story told in the room and the statement that tells a different one.

The advisor who has been there long enough holds something the client eventually loses sight of: the unedited version of themselves.

Not superior knowledge. Continuity. They remember what the client believed before the first big winner. What actually happened. What the client said afterward. What they subsequently forgot. How the pattern repeats.

The client changes the story they tell themselves. The advisor has seen the previous versions.

That is not a small thing to hold. It takes years to build the kind of relationship where someone will show you the statement. Where the silence can be noticed and the question can be asked without it feeling like an accusation. Where the admission, I got lucky, I lacked discipline, can be made without the relationship absorbing a cost it can't recover from.

Every investor has both.

The multibagger and the skeleton. The story told in the room and the one that stays in the account.

The question is whether the version of yourself you brought to those decisions is the one you think you brought.

The account doesn't lie.

It just waits until you're ready to read it that way.

Diptes Basu writes about investing, behavior, and decision-making, drawing on twenty-five years in global financial markets.

This essay reflects the author's personal views and is intended for educational purposes only. It does not constitute investment or financial advice.

The Model We Didn't Choose

They grew up in the same house.

Same parents. Same neighborhood. One year apart in age. Similar schools, similar academic paths, similar circumstances by almost any measure visible from the outside.

By the time they were adults, you would not have guessed they came from the same family.

One was brilliant and isolated. Deeply suspicious of others. Ultra-conservative in almost every decision, financial and otherwise. Money sat untouched rather than deployed. Plans were started and abandoned. Trust was withheld even where it would have helped.

The other was equally brilliant. Social, a connector, a planner. Trusted others without being naive. Made balanced decisions across every domain. Built things deliberately and followed through.

Same household. Completely different people.

I knew both of them well. And I still cannot fully explain the divergence.

But that, I eventually realized, was the more interesting part.

The siblings did not have identical inputs. They had the same household. That is not the same thing.

Birth order. Temperament. Friends. Teachers. Chance events. The way each interpreted the same conversation. What each made of the same parent on a different day. Experiences that one remembered and the other barely noticed.

Much of what shaped them was invisible to me.

The puzzle wasn't that the same inputs produced different outputs.

The puzzle was that I could never see the full input set.

I'm not sure anyone could.

I carried that puzzle into my work without quite realizing it.

Every client who walked into a conversation was carrying a model they had not consciously designed.

Not a financial model. A decision model.

It had been built from everything that happened before the conversation started: the family they grew up in, the first time they lost money, the first time someone they trusted with money let them down, the culture they absorbed around wealth — whether it was something to be protected, spent, feared, displayed, or never discussed.

That model produced outputs I could observe.

The client who couldn't hold cash without immediately investing it. The one who couldn't sell a position even when the numbers argued for it. The one who asked the same question seventeen different ways because they needed to hear the answer seventeen times before anything shifted.

I could see the outputs clearly. The inputs, partially. The process connecting them, almost never.

And over time I noticed something that complicated the usual language of bias.

The model was often not wrong.

The client who couldn't sell a concentrated position had sometimes built significant wealth through exactly that kind of conviction. The instinct that later made diversification difficult was the same instinct that had produced extraordinary returns.

The behavior that looked irrational in one context had been adaptive in another.

The problem wasn't necessarily that the model was defective.

Sometimes the world had changed. The model hadn't.

And when that happens, the model doesn't announce it. It keeps running.

Often, the reasoning comes after.

We experience a decision as the conclusion of analysis, but much of the direction may already have been shaped by the model underneath. The explanation arrives afterward, giving the decision a coherent story.

This isn't a defect unique to investors. It is one of the ways human cognition makes the world manageable. We learn from experience. We recognize patterns. We build shortcuts. We predict what is likely to happen next.

Speed requires shortcuts. Shortcuts require tradeoffs.

The question that stayed with me about the siblings was not why they were different.

It was how little of the explanation was visible even to someone who knew them well.

I began to recognize the same problem in client conversations — and then, years later, AI gave it a name I couldn't ignore.

Interpretability.

AI researchers can inspect what goes into a model and measure what comes out. They can sometimes identify which features influenced an output, trace certain internal patterns, find particular behaviors. But a complete account of why a model produced this output, in this situation, remains extraordinarily difficult.

We spent years calling AI systems black boxes.

Then we began to realize something uncomfortable.

We are too.

Not in the sense that human brains are literally neural networks, or that human cognition works exactly like machine learning. It doesn't.

The parallel is simpler.

Both are systems whose past shapes how they interpret what comes next — and both can encounter situations where those patterns stop working.

The human black box built the machine black box.

And in doing so, reproduced some of the properties that trouble us about our own cognition: learning from experience, pattern recognition, internal representations we cannot easily inspect, imperfect generalization when circumstances change.

We built systems in our own image without quite knowing it.

A decision model can be adaptive when it is formed and quietly maladaptive later.

The investor whose refusal to sell once protected them from panic may eventually mistake persistence for discipline.

The model keeps producing internally consistent answers.

That is precisely the problem.

Internal consistency is not evidence that the model is still describing the world accurately.

The model rarely tells you.

The most dangerous model isn't the one that was wrong. It's the one that was right for a long time.

Perhaps this is where self-knowledge becomes less about understanding yourself completely and more about becoming suspicious of your own certainty.

You don't need to reconstruct every experience that shaped a decision. You probably can't.

You don't need a complete causal account of why you respond to one situation with confidence and another with fear. You may never have one.

But you can notice when the predictions keep failing. When the same decision produces the same disappointing outcome. When evidence that should change your mind somehow never does. When the explanation you give yourself remains remarkably stable while the world around it changes.

That may be the closest thing we have to auditing the model.

Not opening it up completely.

Watching what it predicts.

And noticing when reality keeps disagreeing.

I still think about those two siblings.

Not about what went wrong or right.

About the puzzle.

The same household, the same parents, the same neighborhood — and yet two completely different ways of moving through the world.

I still cannot fully explain it.

Not because I lacked access.

Because a complete explanation would require seeing everything that mattered: every formative experience, every interpretation, every weight placed on every event, every connection between them.

That information was never available to me.

It may not be fully available to them either.

And perhaps that is what makes the comparison with AI uncomfortable.

We are discovering that, in trying to understand machines, we have built a mirror for a problem we have never completely solved about ourselves.

We can observe the output.

We can sometimes reconstruct the inputs.

But somewhere between the two is a process we may never fully see.

We built systems in our own image, it turns out.

More than we realized.

Diptes Basu writes about investing, behavior, and decision-making, drawing on twenty-five years in global financial markets.

This essay reflects the author's personal views and is intended for educational purposes only. It does not constitute investment or financial advice.

Built for the Last Battle

In February 1942 the guns of Singapore faced the sea.

They had been built that way deliberately — heavy artillery pointed outward at the Strait of Singapore, designed to repel the naval assault that everyone assumed would come. The fortifications were formidable. The conviction behind them was absolute.

The Japanese came overland. Through Malaya. From the north.

The guns couldn't turn. In a week it was over. Winston Churchill called it the worst disaster in British military history. Not because the defense was weak. Because it was facing the wrong direction.

I have thought about Singapore often — not the military failure, but the psychological one. The conviction so certain of where the threat would come from that it couldn't update when reality arrived differently.

When I moved from India to the United States I sold every position I held.

Clean break. New chapter. The logic felt unassailable.

What I left behind quietly became worth many times what I carried forward.

I have told myself the peace of mind was worth it. I still tell myself that.

Years later, in the United States, I found myself buying into companies at what turned out to be historic lows. I saw what others had missed. I acted on it. And then — too soon, convinced the run had gone far enough — I got out.

Those positions went on to become something else entirely.

There is one I held. It sits in a tax deferred account — long term by design, withdrawals penalized, mentally labeled untouchable. I held it not because my conviction was strongest there. Because the structure made it hardest to act.

It is still paying.

I tell these stories not because I have solved something. I haven't. I tell them because they are the honest context for everything that follows.

There were two clients. Call them A and B.

Different people. Different temperaments. Remarkably similar situations.

Both held concentrated positions in a single stock — in each case the majority of their net worth. Both had built significant wealth through that concentration. Both received the same professional advice: reduce the position systematically, tax-efficiently, before the concentration became the risk.

B didn't move.

I know this company better than anyone — B said. I've been behind the wheels. I know what it's worth.

The conviction was genuine. B probably did know the company better than most. The analysis was real. The certainty was earned — forged over years of watching the company grow, of being right when others doubted, of building something meaningful through sustained belief.

B leveraged to buy other assets.

When the stock fell — dramatically, as concentrated positions sometimes do — the margin calls arrived. The forced selling began. The financial life that had been carefully constructed had to be rebuilt from a position nobody had anticipated.

A sold.

Systematically. Tax-efficiently. At a pace that felt almost anticlimactic given what was at stake.

When I asked A about it afterward the answer was simple.

I never quite believed I deserved all of it — A said. The company did well. I was there. But I wasn't the only reason.

Gratitude. That was the word A used.

I have spent a long time thinking about the difference between A and B.

Not the financial difference. The psychological one.

B had learned — correctly, from real experience — that conviction pays. That holding firm when others sell is the strategy that works. That knowing a company deeply is an edge worth trusting.

Those lessons were true. They were earned. They produced results.

But they were calibrated for a specific kind of threat. A falling market. Nervous colleagues. Pressure to diversify before it was necessary.

They were not calibrated for the moment when the conviction itself became the threat.

Once B owned the stock — had worked for the company, received it as compensation, watched it appreciate over years — it stopped being purely an asset. It became part of the story of how B got here. Selling felt like losing something that wasn't only financial.

And then the evidence began contradicting the conviction.

B's mind didn't update the conviction. It discredited the evidence. The stock was down? The market was wrong. The analysis said sell? The analysis didn't understand the business.

The conviction didn't update.

It relocated.

Assets moved to where no one could intervene. Where the conviction had space to breathe without contradiction. Where the guns could keep facing the direction they had always faced.

A's gratitude wasn't weakness.

It reflected an unusually simple recognition — I didn't fully control how I got here, so I shouldn't assume I fully control what happens next.

Perhaps that's why selling didn't feel like self-betrayal.

B's conviction was the mirror image. The gain was entirely B's — the product of superior knowledge, superior judgment, sustained commitment. Selling would have meant admitting the conviction was partially wrong.

The armor B had built — genuinely protective for years, genuinely earned — had become the thing that held B in place while the world moved on.

The guns were still facing the sea.

I don't tell these stories — mine or theirs — to suggest there is a formula for getting this right.

There isn't.

A had conviction too. A's conviction was simply held loosely enough to update. My best performing position was held not through superior discipline but through a structure that made acting on impulse harder than sitting still.

The line between wisdom and luck, between discipline and friction, is thinner than most financial narratives acknowledge.

What I notice — in clients, in markets, in myself — is that the convictions most worth examining are rarely the ones that feel uncertain. They are the ones that feel unquestionable. The ones that have stopped being positions and become identities. The ones where contradicting evidence doesn't prompt reconsideration — it prompts reorganization.

That reorganization — quiet, logical-feeling, entirely self-justifying — is the armor doing its work.

Every adaptation eventually becomes a constraint.

The question is whether you discover that by reflection — or by consequence.

Every one of us builds defenses against yesterday's uncertainty.

The question is whether, when tomorrow arrives, our guns are still facing the sea.

Diptes Basu is a behavioral finance writer and founder based in Delhi. He writes about investing, behavior, and what twenty-five years in global markets taught him about how people actually make decisions.

This article is for informational and educational purposes only. It does not constitute financial, investment, or professional advice. The experiences and observations described reflect the author's personal perspective and are not intended as recommendations for any specific investment strategy or course of action. Past outcomes are not indicative of future results. Readers should consult a qualified and registered financial advisor before making any investment decisions.