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Reducing Risk When Buying Shares in a Company

How can I manage risk when investing? Can risk be controlled by an investor? What are ways I can reduce risk in my investments? These are questions that might be at the back of your mind. I share my views on risk and how understanding intrinsic value and applying a margin of safety reduces that risk.

Hello and welcome to your weekly Lockstep Investing Newsletter.

This week, we cover the following:

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Investing is hard and the best way to improve your own investing is through others. So, under “Investing Chronicles”, I’ll share my learnings from my 18+ years in the stock markets.

How can I manage risk when investing? Can risk be controlled by an investor? What are ways I can reduce risk in my investments? These are questions that might be at the back of your mind.

I want to share my perspective on risk, which, while not unique, diverges from conventional thinking and is, more importantly, NOT intuitive.

Understanding and Reducing Risk When Investing

What Risk Isn’t

In its purely theoretical form, risk is the volatility of a share price. The more a share price fluctuates, the riskier it is perceived to be.

I disagree with this concept!

Share price volatility is more a measure of emotional stimulus than risk – we become depressed and anxious when the share price moves significantly below our purchase price and exuberant when the share price rises above. But mood swings are not risk!

How I Perceive Risk

In investing, the risk is that we lose money; we lose money when we are forced to sell our investment at substantial losses.

Therefore, to better understand risk, we need to understand what it is we are trying to do so that we can reduce making big mistakes;

What is Investing Actually

In its essence, investing is laying out cash today with the expectation of getting more back sometime in the future. We are, therefore, occupied with trying to answer 3 fundamental questions:

  1. How much cash will I get back?

  2. When will I get it back?

  3. How CERTAIN am I of getting it back?

The better I can answer these questions, the greater the probability of a successful outcome and the less RISK I have of losing money. But the opposite holds too in that:

LESS certainty = MORE risk

Intrinsic value: What is it?

To answer the questions above let’s work an example together:

We are considering purchasing a company, The Once-ler Company, which manufacturers Thneeds (borrowed from The Lorax 😉). We are fortunate to have a crystal ball to know that Thneeds will be in fashion for exactly 10 more years before no one buys one ever again. Furthermore, our crystal ball gives us perfect foresight regarding the company’s future cash generation:

Thanks to this foresight, we know that Once-ler will generate $1000 in cash over its remaining lifespan. However, as cash received tomorrow is worth less than cash in hand today, we discount these future cash flows back to their present value—let’s use a 5% discount rate for simplicity:

So we now know that Once-ler will produce $1000 in the future, equivalent to $803 in the bank today (based on our 5% discount assumption).

The $803 is the company’s intrinsic value and is what we are trying to calculate when we invest. If someone offered to sell you the business for $850, you would turn it down, knowing you would lose money, but if offered $750, you would happily buy it, knowing you were earning a $53 profit.

Intrinsic Value and the Real World

Unfortunately, in reality investing isn’t that simple. I do not know what the cash flow of The Once-ler Company will be. I don’t know how long it will remain in business. I don’t know how competent management is or what the competition will do. I have to, therefore, estimate what I believe intrinsic value to be based on certain assumptions.

Of course, the more assumptions I have to make, the more my uncertainty increases, and we know from above uncertainty = RISK.

Unfortunately, even if we do all our homework, there will still be much we don’t know.

So, how do I reduce risk?

Intrinsic Value is Not a Number but a Range

We can reduce our risk by increasing the expectations of the possible outcomes for intrinsic value.

Instead of trying to guess a single number and declare the Once-ler company is worth $803, we can look at our assumptions and apply best and worst-case scenarios to our estimates.

The best-case scenario is when we factor everything runs perfectly, and the company is worth $850. The worst case is the opposite, and Once-ler experiences nothing but headwinds, producing only $750 worth of cash in present-value terms. So, instead of saying the company is worth $803, we estimate it to be worth anything from $750 to $850.

But we can reduce risk further still.

Risk and the Margin of Safety

Let’s delve into the concept of the margin of safety, a term often encountered in investment discussions. While I’ve touched upon it briefly in a previous newsletter, let’s explore it more deeply here;

Returning to the Once-ler company - after all our hard work and analysis, we estimate it is worth between $750 and $850.

So, would I actually buy it for $750? Probably not, because what if my calculations are wrong (and they definitely will be no matter how good an analyst I am) and I have overstated the value? It might only be worth $700; I would have lost money.

But what happens if the market panics, for whatever reason, and someone is offering to sell me Once-ler for $500? I would now have a safety net if my calculations were wrong and the company only produced $700 or even $600 worth of cash.

The larger the safety net, the wider my Margin of Safety and the LOWER THE RISK.

(Companies can actually be offered at massively discounted prices; just look at when Meta Platforms (META) traded at under $100 per share because the market panicked .)

Risk and the Share Price

You might have noticed that in our discussion thus far, we have not mentioned the share price. That is because, if you agree with my concept of risk above, it has little to do with the company’s share price.

The share price is simply the price of the most recent transaction between the buyer and the seller of a share. It has nothing to do with what a company is worth – the seller believes the company is worth less, or they wouldn’t sell, and the buyer thinks it to be worth more – but just because they believe it doesn’t make it so.

But we know better and can take advantage of this!

We now know that a falling share price implies our Margin of Safety is increasing, and therefore our risk is REDUCING. Conversely, a rising share price means my risk is INCREASING because my margin of safety is diminishing.


My task as an investor is to figure out:

  1. How much cash I expect to get back in the future,

  2. When I expect to get it back, and

  3. My level of confidence it will happen.  

I cannot accurately calculate how much cash I will get back, so I estimate a range of the intrinsic value using differing scenarios.

To provide an additional safety net, I invest when the share price is lower than that range.


  • When the share price retreats, my margin of safety increases, so my willingness to buy more shares increases.

  • When the share price appreciates, my margin of safety diminishes, and I become more inclined to sell.

Hopefully that gives you a better understand of risk, at least how I perceive it. And perhaps you even agree!


There is no faster way to learn about investing than through the Greats. Here, I share lessons from the best investors and thinkers.

I want to introduce you to the well-regarded value investor, Mohnish Pabrai and his book “The Dhando Investor: The Low-Risk Value Method of High Returns”.

Mohnish’s Background

Mohnish Pabrai is a seasoned investor and the founder of Pabrai Investment Funds, which he started in 1999 after a career as a software engineer. Although I cannot find published returns, sources report his fund has returned over 20% per year.

While it is challenging to verify these returns, his fame as an investor and his proximity to Warren Buffett and his idol, the late Charlie Munger, suggest he knows what he is talking about.

Dhando Investing and Risk

While the book about Dhando investing covers several topics around value investing, what stood out for me, and in line with today’s Investing Chronicle, is Pabrai’s approach to risk:

“Heads I win, Tails I don’t lose much”

Mohnish Pabrai

This beautifully articulated phrase encapsulates the core principle of managing risk – make sure your downside is limited so that you don’t lose the shirt off your back if you are wrong. But if you are right, you can do very well for yourself.

You Won’t Always Be Right

Pabrai also clarifies that he doesn’t expect to be right all the time. In fact, he believes his success rate is only around 60%. If this seasoned pro only expects 6 out of 10 of his investments to go his way, then we shouldn’t expect to do much better.

But you don’t need to always be right, but it is so crucial that our downside is limited because, for the 40% or more we are wrong, we need to ensure our losses are limited such that we “don’t lose much”.

How do we do that?

Central to Pabrai’s philosophy is the concept of a margin of safety, which you are now acquainted with. His approach is to buy stocks at a significant discount to their intrinsic value, providing a buffer against potential losses. Sound familiar!

The good news is that you now know how to do that!


Whether you’re a seasoned investor or a novice seeking to build wealth, “The Dhandho Investor” is a great read. It presents the concepts of value investing in a very easy-to-understand format, leaving you with more confidence in your ability to be a successful investor.

He also has regular blog posts or perhaps you would prefer his interviews.

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