Chapter 2 of 9 · 6 min read

Understanding and Measuring Risk

How statistics turns future return uncertainty into a concrete number called Volatility, and why two investments with the exact same performance can demand very different capital allocations.

We all have an intuitive idea of what risk means: we associate risk with loss. Another way of looking at Risk is the amount of uncertainty of future returns, which we can estimate from an investment's past returns. Casinos pose a very high risk for most people since the odds of winning are highly random. Investing in a Savings Account or short-term Treasury Bills is low risk (close to zero) because the return is predictable and backed by institutions in a stable country.

Interestingly, this uncertainty can be expressed using the field of statistics through concepts like Volatility. Volatility refers to the bumpiness or fluctuations in returns. It is also termed the Standard Deviation of Returns if you are familiar with high school statistics. It is a foundational measure of risk which, while not perfect, gives us a strong relative sense of risk across different investments.

In general, the higher the volatility, the greater the fluctuation or uncertainty in returns. Investors should prefer lower volatility to higher volatility, unless the performance is correspondingly higher for the more volatile asset, which we will illustrate in Chapter 4.

Example: Same Performance, Twice the Volatility

The following example from real market history shows two investments that achieved the exact same 5-year performance (+123%), but with very different return paths and volatility. Note that this is always possible: for the exact same final performance, we can have an endless number of return combinations. Think about the implications of that. Many investors never do.

Line chart comparing Investment 1 (Cintas, +123% return, 23.4% volatility) and Investment 2 (Netflix, +123% return, 43.3% volatility) from October 2020 to October 2025
Figure 2.1: Which One Would You Prefer? Both Have the Same Performance (+123%), But Investment 2 Has Nearly Twice the Volatility. Starting with $100 in October 2020, Investment 1 (Cintas, CTAS, 23.4% volatility) and Investment 2 (Netflix, NFLX, 43.3% volatility) both finished at $223 in October 2025. Yet Investment 2 subjected investors to nearly twice the volatility and a brutal -76% crash mid-journey.
Explore this exact pair interactively in EasyCompare:

If you look at the price evolution and its bumpiness in Figure 2.1, Investment 2 is much more volatile than Investment 1 (nearly twice as volatile: 43.3% vs. 23.4%). In general, investors would prefer Investment 1 if you only want to invest in one. But there is room for both investments in a portfolio as long as we allocate our money accordingly.

One practical approach is to balance allocation according to risk and performance. In this case, since Investment 2 has roughly twice the volatility for the same performance, you may choose to allocate half the amount to Investment 2 as you allocate to Investment 1 as a rough heuristic. This is a great starting point, though other factors also come into play including your fundamental views and reward-to-risk profiles, which we will discuss in Chapter 4.

Try Risk-Balanced Capital Sizing

Click any real pair of investments below that achieved the exact same 5-year return (Oct 2020 to Oct 2025), and see how a volatility-balanced heuristic splits your capital between them:

CTAS: Cintas Corp (Investment 1)

+123.4% total return
23.4% annual volatility (-23.8% max drop)
$6,492 (65%)
Recommended Risk-Balanced Allocation

NFLX: Netflix, Inc. (Investment 2)

+123.0% total return
43.3% annual volatility (-75.9% max drop)
$3,508 (35%)
Reduced Allocation (Nearly 2x Volatility)

Open Pair in EasyCompare (2020–2025) → Open Pair With Latest 5Y Data →

Volatility of Different Assets Varies Wildly

Volatility is one of the most important concepts you can understand in investing. You do not need to know how it is computed mathematically, but an intuitive sense of volatility will help you look at different investments in a completely new way. To cement this risk measurement, the chart and table below show the 5-year annualized volatilities of familiar investments across asset classes.

Horizontal bar chart showing 5-year annualized volatility across US Treasury Bills, S&P 500, Amazon, S&P 500 in 2008, NVIDIA, Tesla, and Bitcoin
Figure 2.2: Volatility of Different Assets Varies Wildly (Oct 2020 to Oct 2025, plus S&P 500 in 2008). Volatility ranges from 0.3% for US Treasury Bills and 17.3% for the S&P 500 index, up to 35.0% for Amazon, 52.3% for NVIDIA, 61.3% for Tesla, and 69.4% for Bitcoin Trust.
Compare these volatilities interactively in EasyCompare:

As you can see, volatilities vary widely, showing how much uncertainty differs across individual stocks and asset types. They can even rise above 100% (for example, 3x leveraged ETFs like SOXL had 105.3% annualized volatility over this same 5-year period, and Litecoin reached 116% in our 2018 edition). In fact, there is no upper limit to volatility, though it can never be infinite.

Cryptocurrencies and high-growth single stocks show remarkably higher levels of volatility compared to broad market indices, which aligns with everyday intuition. We recommend that you memorize a few of these benchmark volatilities so you always have a frame of reference in mind when evaluating any investment. The S&P 500's long-term average volatility (~13% to 17%) is especially useful as your baseline anchor. During the 2008 financial crisis, the S&P 500's volatility spiked all the way up to 41% to 43%1.

Investment Category 5Y Volatility (2020–2025) 2018 Edition (5Y) Multiple of S&P 500 Risk
US Treasury Bills (SGOV) Cash-Like Benchmark 0.3% ~0.2% 0.02x (Near Zero)
S&P 500 Index (SPY) US Stock Market Benchmark 17.3% 12.9% 1.0x (Reference Anchor)
Amazon (AMZN) Large-Cap Tech Stock 35.0% 30.4% 2.0x S&P 500
S&P 500 in 2008 Crisis Market Crash Regime 41.4% (up to 43%) 43.0% 2.4x Normal S&P 500
NVIDIA (NVDA) Semiconductor Growth Stock 52.3% 38.1% 3.0x S&P 500
Tesla (TSLA) Volatile Single Stock 61.3% 44.3% 3.5x S&P 500
Bitcoin (GBTC / BTC) Cryptocurrency 69.4% 77.0% 4.0x to 6.0x S&P 500

How can you get an even more intuitive, everyday sense of volatility that is easy to remember and apply on the fly? The next chapter is devoted to that.