moontower: a stoner dad explains options trading to his kids

moontower: a stoner dad explains options trading to his kids

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Kris Abdelmessih's avatar
Kris Abdelmessih
Jun 11, 2026
∙ Paid

Friends,

In a random walk where trials are independent, variance scales linearly with time. Since standard deviation is the square root of variance, volatility scales with sqrt(T).

This sublinear power law scaling gets smuggled into option math that answers practical questions. For example, assuming implied vol is constant, a 12-month ATF straddle is twice the price of a 3-month ATF straddle because sqrt (12/3) = 2.

This scaling is commonly used to convert raw vega into weighted vega. Raw vega is an extremely low-resolution number. If you own 50k 12-month vega vs being short 40k 3-month vega then it appears like you are long vol. But 12-month IV doesn’t whip around as much as 3-month IV, so this position will not act like it’s long vol on a large move higher in vol as the term structure will not “parallel shift” higher. The 3-month will increase faster as the term structure steepens into a downward sloping shape. A shape referred to as “inverted” or “backwardated”.

A simple way to modify raw vega is to scale all your monthly vegas by 1/sqrt(T) by normalizing them to a fixed DTE, for example 3 months. In that case, using the same math we did above, a 12-month vega is cut in half relative to the 3-month.

So your re-weighted vega is now short 15k vega instead of being long 10k vega!

12-month vega x scaling factor relative to 3m vega = +50k * 1/sqrt(12/3) = +25k

3-month vega x scaling factor relative to 3m vega = -40k * 1/sqrt(3/3) = -40k

Net: -15k

That volatility changes should move in proportion to 1/sqrt(T) is not a commandment brought down from Moses. It’s a convenient scaling factor that corresponds better, even if imperfectly, to empirical vol surface behavior. It also has a handy interpretation. If IV’s change in proportion to 1/sqrt(T) then ATM time spreads are unchanged (net of theta). In other words, the 3m/12month straddle spread is unchanged in such a regime.

Again, this scaling doesn’t need to hold. Sometimes we have parallel shifts in term structure and sometimes term structures steepen faster or slower than sqrt(T) scaling would predict. But the scaling is still a better prediction than the raw vega measure, which would have you believe IVs from all months are directly comparable without adjusting for how slow long-dated IVs change or how fast a weekly IV can move.

Random walks and the derivative pricing theory built upon them assume returns are independent. In hindsight, random walks still exhibit stretches that can be labeled “trend” (like a run of heads) or “mean reversion” (period of frequent alternating). But it’s one thing to label these stretches and hindsight vs predict them.

It should be self-evident that being able to predict trends or reversion would be marvelously profitable for a directional trader. But, direction aside, it would be a gift to volatility traders as well. It would influence not only how they priced vertical spreads and time spreads but the deltas in their models and their delta-hedging strategies. In other words, it would change everything if you had an edge on the probability of the next move being up or down, even if you did not have an edge on the fair value of the stock (this would occur if you had an edge on probability but not on the magnitude of up move vs down move). Option structures allow fine-grained bets that can isolate probability from magnitude.

If an asset trends over weeks or months, you will underestimate its volatility by scaling its daily volatility by sqrt(T). That makes sense. If it trended, that’s similar to saying the moves were auto-correlated and therefore dependent. Again, this is descriptive, not predictive, but relating measures of volatility to this interdependence lets us see how sensitive option pricing is to the random walk assumption. A few articles I’ve written in this vein:

  • how a high implied vol can be cheap | 9 min read

  • The Option Market’s Point Spread (Part 2) | 11 min read

  • Thinking In N not T | 6 min read

These articles have a unifying concern. If prices are random, then sure, the power function that specifies how volatility scales is the familiar:

\(\begin{aligned} \sigma_T &= \sigma_1 \cdot T^{1/2} \\[8pt] \text{where} \quad \sigma_T &= \text{vol over the horizon} \\ \sigma_1 &= \text{daily vol} \\ T &= \text{time to expiry (trading days)} \end{aligned}\)

But if prices trend or mean-revert, the exponent is no longer 1/2.

\(\begin{aligned} \sigma_T &= \sigma_1 \cdot T^{H} \\[8pt] \text{where} \quad \sigma_T &= \text{vol over the horizon} \\ \sigma_1 &= \text{daily vol} \\ T &= \text{time to expiry (trading days)}\\ H &= \text{scaling factor} \end{aligned}\)

Over any historical sample, H can be observed to be something other than 1/2. For it to be 1/2 would mean that annualized volatility over 2 different sampling windows was identical. In hindsight, that will rarely occur. But it’s also true for any exponent you pick. It’s hard to make the persistent case for a value other than 1/2, especially when it carries the financial totem of randomness.

In Retail Options Trading, Euan Sinclair says markets aren’t random, but they’re close to random. The question of whether there’s enough life growing in the gap between “random” and “almost random” for a skilled hunter to eat is existential professional investors’ careers.

We need to examine randomness.

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