appreciating diversification

This week, I hosted class #4 of the Investment Beginnings for local kids aged 12+.

The series’ materials are here:

https://notion.moontowermeta.com/investment-beginnings-course

This is the specific material for class #4:

I also created a web version of the game:

☀️🌧️Sun/Rain Game

While I’ve been doing the series for kids, I think a lot of adults could even benefit. The overall arc of the presentation:

  1. Last class’s game ended with a humbling but common result, hinting at a key pillar of investing.
  2. We use a few facts to dispel the recency bias that all investors carry with them.
  3. They learn what the fundamental nature of stocks predicts about their individual and group behavior.
  4. We widen the meaning of diversification beyond stocks, which was extremely easy to do in light of March 2026.
  5. We play a game that makes the implications for portfolios concrete.

While moontower readers span a wide range of investment experience (although overall quite interested in investing and money), here are a few ideas that I hope are presented in ways that might augment even your understanding or at least help you explain to learners in your life.

The most naive strategy is hard to beat

The kids spent Class 3 picking stocks based on a bunch of variables they could sift through, only for the equal-weight benchmark to beat everyone except the team that contrarily concentrated in the highest momentum company that is very much still an enigma to the market (TSLA).

The equal-weight strategy which I just called a monkey (although it’s not random, just dumb) beat 2/3 of the 15 individual stocks themselves.

The reason you shouldn’t be surprised that the naive strategy is hard to beat

Companies eventually die, but indexes shed them before they are in hospice.

Only 17% of the original S&P 500 companies from 1957 survived 50 years. The average company lifespan on the index was 33 years in 1964 — it’s now under 20. Kodak invented the digital camera in 1975 and buried it because of the innovator’s dilemma.

In a crash, stocks remember they’re all stocks.

Diversification works differently in good years than bad ones. In the class data, stocks spread widely in bull years. Then we looked at Jan 2022 to Jan 2023: 13 of 15 stocks fell together, the spread collapsed.

I didn’t want to lean into the word correlation, but I noticed a different way to convey the same idea. The inter-quartile range (IQR) of annual returns was smallest in the worst years. This chart is rich with insight. Notice the IQR’s visually but also how the equal-weight portfolio performed relative to the individual stock and median stock returns each year:

These observations are non-CAPM ways to arrive at the familiar language of diversifiable risk (company-specific stuff you can eliminate for free) and systematic risk (market-wide stuff you can’t diversify away but do get paid to carry). The crash revealed which was which.

If we zoom out from stocks alone, we see a race where the leaders change each year

The Novel Investor quilt shows 15 years of annual returns ranked best to worst across 9 asset classes. The diversified portfolio, that gray-ish bar, never wins a year nor comes in last. Note commodities, gold and BTC are absent from the series.

How do you think they would influence the gray portfolio?

The Sun/Rain Game

This leads to a game where we can build some intuition about the role of non-stock assets in a portfolio.

If you look at the sheet you can see how the kids actually did (I changed the kids names to letters):

The game’s punchline is that owning the anti-correlated asset despite it having a worse expected return than the “good” asset leads to a better long-term portfolio.

But this is so unintuitive that I got a student’s question wrong during the discussion!

I’ll explain the mistake here.

A student asked if we played the game for 100 years instead of just 20 years, if owning the good asset ONLY would have led to the best return. I initially said no, then corrected myself and said yes because it has the higher expected return.

But I was right the first time. The answer is definitely NO.

It comes down to the fact that the good asset has an expected arithmetic return of +5%, BUT it has a negative expected CAGR or geometric return.

The math:

The company is 50/50 to return+40% or -30% in any given year.

.5 x 40% + .5 x -30% = +5%

But over 2 years, you expect 1 up, 1 down. Compounding math:

1.4 x .7 = 98%

You expect to lose 2% over a 2-year sequence of about 1% per year.

Formally, we compute the expected CAGR by multiplying (note how the arithmetic or single period return is added):

1.4^(1/2) * .7^(1/2) – 1 = .9899 -1 = -1%

[The exponents represent the probability of each outcome. If there were 3 outcomes, you’d have 3 terms and the exponents sum to 1.]

In the long run, the good asset destroys value. So you do not want to concentrate in it despite its superior expected arithmetic return.

The CAGR is being killed by volatility drag, which is the asymmetry of the fact that if you lose 30% you need to return 42.9% to get back to even, but the “up” years only return 40%. You are falling behind over time.

The bad asset returns -10% half the time and +8% half the time. It’s a “worse” asset, but it’s less volatile. Taking this quality to its extreme, isn’t this what cash is?

In arithmetic terms, our average return if we allocate to each asset equally is +2% (50% x 5% + 50% x -1%). But that portfolio is less volatile because one stock zigs when the other zags. The diversification cuts the volatility MORE than it cuts the expected return, leading to a better risk/reward!

If we rebalance each year back to an equal-weight portfolio, we “pull” the expected CAGR closer to the expected arithmetic return. It’s the only way we can get close to eating those expected arithmetic returns. Otherwise, they don’t really exist for you over time.

This table is worth staring at:

Here’s a message one of the dads sent me after the class:

Measure Your Own Diversification

I made you a tool to compute your portfolio vol and see how much the cross-correlations between your holdings have been reducing total vol from the vol that the individual assets contain. You can tinker by adding ETFs of other asset classes to your equities (ie GLD or USO or TLT etc) to see how they affect the volatility.

If you just want inspiration for an idea, use the tool to compare the Mag 10 index (MGTN) realized volatility with the average realized volatility of its holdings. The index is conveniently equal-weighted, 10% in each name.

Two ways to try this on your own portfolio:

🌐To run in your browser

https://colab.research.google.com/github/Kris-SF/data-pipelines/blob/main/portfolio-vol/portfolio_analysis.ipynb

⚠️Just push through the warning it spits off

The output will includes metrics and charts:

 

🖥️To run locally

git clone <https://github.com/Kris-SF/data-pipelines.git>
cd data-pipelines/portfolio-vol
pip install -r requirements.txt
jupyter lab portfolio_analysis.ipynb

Either way, edit the WEIGHTS dict and the START / END dates, then Run All.

Moontower #313

In this issue:

  • The “three pitches” rule and a lazy man’s framework for getting in shape
  • Things that popped from the Investment Beginnings Lesson #4 — Risk
  • Made you an easy online tool to see how much diversification benefit you get from your holdings

Friends,

A couple of good articles that stood out before we get to Money stuff.

How to Apply Pixar’s “Three Pitches” Rule | 3 min read

David Epstein spent a lot of time with Ed Catmull in researching his recent book Inside the Box. He shares a neat practice from Pixar. Directors aren’t allowed to bring one idea, they must develop three. We often fixate on our first idea even though it’s usually not our best (the “creative cliff illusion”). Epstein applied this in writing the new book by writing three different openings for every chapter. Nine of twelve chapters ended up using attempt #2 or #3. He admits this is tedious, but leads to better quality. I’d add that LLMs can ease some of that burden or augment the process by asking them to consider more ideas beyond the 3 you generate yourself.

The Lazy Man’s Guide to Actually Getting in Shape | 60 min read

Jonathan doesn’t publish often these days, but it’s worth subbing; otherwise, you’ll miss a treatise like this. This is 16,000 words, but Jon tells you upfront that you can just read the bolded sentences for a fast version. It’s a moneyball lens on fitness with a decision process that generalizes to any wicked domain, wellness, of course being one of the most wicked. A lot of examples of “think in probabilities”, “make +EV bets with limited downside”, “via negativa”, and toggling confidence when multiple lenses validate an idea (ie personal experience, expert track record, math, what works empirically, science).


Money Angle

This week, I hosted class #4 of the Investment Beginnings for local kids aged 12+.

The series’ materials are here:

https://notion.moontowermeta.com/investment-beginnings-course

This is the specific material for class #4:

I also created a web version of the game:

☀️🌧️Sun/Rain Game

While I’ve been doing the series for kids, I think a lot of adults could even benefit. The overall arc of the presentation:

  1. Last class’s game ended with a humbling but common result, hinting at a key pillar of investing.
  2. We use a few facts to dispel the recency bias that all investors carry with them.
  3. They learn what the fundamental nature of stocks predicts about their individual and group behavior.
  4. We widen the meaning of diversification beyond stocks, which was extremely easy to do in light of March 2026.
  5. We play a game that makes the implications for portfolios concrete.

While moontower readers span a wide range of investment experience (although overall quite interested in investing and money), here are a few ideas that I hope are presented in ways that might augment even your understanding or at least help you explain to learners in your life.

The most naive strategy is hard to beat

The kids spent Class 3 picking stocks based on a bunch of variables they could sift through, only for the equal-weight benchmark to beat everyone except the team that contrarily concentrated in the highest momentum company that is very much still an enigma to the market (TSLA).

The equal-weight strategy which I just called a monkey (although it’s not random, just dumb) beat 2/3 of the 15 individual stocks themselves.

The reason you shouldn’t be surprised that the naive strategy is hard to beat

Companies eventually die, but indexes shed them before they are in hospice.

Only 17% of the original S&P 500 companies from 1957 survived 50 years. The average company lifespan on the index was 33 years in 1964 — it’s now under 20. Kodak invented the digital camera in 1975 and buried it because of the innovator’s dilemma.

In a crash, stocks remember they’re all stocks.

Diversification works differently in good years than bad ones. In the class data, stocks spread widely in bull years. Then we looked at Jan 2022 to Jan 2023: 13 of 15 stocks fell together, the spread collapsed.

I didn’t want to lean into the word correlation, but I noticed a different way to convey the same idea. The inter-quartile range (IQR) of annual returns was smallest in the worst years. This chart is rich with insight. Notice the IQR’s visually but also how the equal-weight portfolio performed relative to the individual stock and median stock returns each year:

These observations are non-CAPM ways to arrive at the familiar language of diversifiable risk (company-specific stuff you can eliminate for free) and systematic risk (market-wide stuff you can’t diversify away but do get paid to carry). The crash revealed which was which.

If we zoom out from stocks alone, we see a race where the leaders change each year

The Novel Investor quilt shows 15 years of annual returns ranked best to worst across 9 asset classes. The diversified portfolio, that gray-ish bar, never wins a year nor comes in last. Note commodities, gold and BTC are absent from the series.

How do you think they would influence the gray portfolio?

The Sun/Rain Game

This leads to a game where we can build some intuition about the role of non-stock assets in a portfolio.

If you look at the sheet you can see how the kids actually did (I changed the kids names to letters):

The game’s punchline is that owning the anti-correlated asset despite it having a worse expected return than the “good” asset leads to a better long-term portfolio.

But this is so unintuitive that I got a student’s question wrong during the discussion!

I’ll explain the mistake here.

A student asked if we played the game for 100 years instead of just 20 years, if owning the good asset ONLY would have led to the best return. I initially said no, then corrected myself and said yes because it has the higher expected return.

But I was right the first time. The answer is definitely NO.

It comes down to the fact that the good asset has an expected arithmetic return of +5%, BUT it has a negative expected CAGR or geometric return.

The math:

The company is 50/50 to return+40% or -30% in any given year.

.5 x 40% + .5 x -30% = +5%

But over 2 years, you expect 1 up, 1 down. Compounding math:

1.4 x .7 = 98%

You expect to lose 2% over a 2-year sequence of about 1% per year.

Formally, we compute the expected CAGR by multiplying (note how the arithmetic or single period return is added):

1.4^(1/2) * .7^(1/2) – 1 = .9899 -1 = -1%

[The exponents represent the probability of each outcome. If there were 3 outcomes, you’d have 3 terms and the exponents sum to 1.]

In the long run, the good asset destroys value. So you do not want to concentrate in it despite its superior expected arithmetic return.

The CAGR is being killed by volatility drag, which is the asymmetry of the fact that if you lose 30% you need to return 42.9% to get back to even, but the “up” years only return 40%. You are falling behind over time.

The bad asset returns -10% half the time and +8% half the time. It’s a “worse” asset, but it’s less volatile. Taking this quality to its extreme, isn’t this what cash is?

In arithmetic terms, our average return if we allocate to each asset equally is +2% (50% x 5% + 50% x -1%). But that portfolio is less volatile because one stock zigs when the other zags. The diversification cuts the volatility MORE than it cuts the expected return, leading to a better risk/reward!

If we rebalance each year back to an equal-weight portfolio, we “pull” the expected CAGR closer to the expected arithmetic return. It’s the only way we can get close to eating those expected arithmetic returns. Otherwise, they don’t really exist for you over time.

This table is worth staring at:

Here’s a message one of the dads sent me after the class:

 


Money Angle for Masochists

I made you a tool to compute your portfolio vol and see how much the cross-correlations between your holdings have been reducing total vol from the vol that the individual assets contain. You can tinker by adding ETFs of other asset classes to your equities (ie GLD or USO or TLT etc) to see how they affect the volatility.

If you just want inspiration for an idea, use the tool to compare the Mag 10 index (MGTN) realized volatility with the average realized volatility of its holdings. The index is conveniently equal-weighted, 10% in each name.

Two ways to try this on your own portfolio:

🌐To run in your browser

https://colab.research.google.com/github/Kris-SF/data-pipelines/blob/main/portfolio-vol/portfolio_analysis.ipynb

⚠️Just push through the warning it spits off

The output will includes metrics and charts:

 

🖥️To run locally

git clone <https://github.com/Kris-SF/data-pipelines.git>
cd data-pipelines/portfolio-vol
pip install -r requirements.txt
jupyter lab portfolio_analysis.ipynb

Either way, edit the WEIGHTS dict and the START / END dates, then Run All.

 

An Explicit Solution to Black-Scholes Implied Volatility | Wolfgang Schadner

For the past 50 years, implied vols were calculated from option prices and other option inputs numerically. Simple versions use Newton-Raphson or bisection searches. The idea is to “guess” what the implied vol is, call that g*, see what option price that produces, split the difference, and repeat the recipe until you arrive at a price that is within a fraction of a cent of the market price. This method is used because there’s no closed form going from price → vol, only vol → price.

This SSRN paper came out this week and made the rounds quickly. It offers a closed-form approximation, alleging it recovers IV to machine precision ~3.4x faster than the current best-in-class. If it holds up under wider testing in the wild, it’s the kind of thing that ends up in textbooks.


From My Actual Life

My youngest turned 10 yesterday. I wrote him a letter just as I did for my eldest when he turned 10. It can be hard to remember what your kids are like at every phase. But also, it can be hard to remember where you’re at mentally at those ages. You hope the letter becomes a gift they cherish when they are older and can relate to being an adult writing to their child. But looking back at the letter myself will be a time capsule gift for my future self too.

This is an instance of a belief I have come around to as they’ve gotten older. A lot of what I think I do for them I really think is for me. I want to be around them selfishly more so than I think my presence is as important as I’d like to believe.

The possibility that kids do more for you than you for them is better left as a self-effacing end to having children rather than something to weigh before having them. Don’t tell the optimization maxxers.


This Week In The Options Trench

📺Convexity vs Leverage

This week Eirk and I disentangle the source of amplified profits and losses


Stay groovy

☮️

 

Moontower Weekly Recap

how a high implied vol can be cheap

EWY, the South Korea ETF, was an interesting source of disagreement in our Discord about whether the vol was expensive or not. This is the IV vs trailing RV:

Based on realized vol calcs using daily sampling, IV approaching 50% looks rich.

But EWY had been grinding up since the beginning of the year. (It tanked along with the dollar this week after the Iran strikes.)

 

It was up 25% in February alone.

If we annualize that to a vol:

25% * √12 = 87% vol

More than 2x the realized vol and significantly higher than the “rich”IV.

The posts below discuss this sampling issue from several angles.

  • Risk Depends On The Resolution | 4 min read
  • Volatility Depends On The Resolution | 5 min read
  • The Option Market’s Point Spread (Part 2) | 11 min read
  • Thinking In N not T | 6 min read
  • A Misconception About Harvesting Volatility | 3 min read
  • The Coastline Paradox in Financial Markets | 11 min read

There’s no single “realized” volatility. Every time you delta hedge you sample a unique volatility such that is possible for a long delta hedger and a short delta hedger to both make or both lose money depending on the timing and size of their hedges.

Because we are cursed with memories, every good trade we do, we wish we did bigger, and every bad one we wish we did none of. Our memories, combined with the noise inherent in delta hedging is a recipe for madness. That’s why all option traders are unpleasant and wish they had chosen a career where they can simply clip a fee from the collective net worth of society, which has been steadily levitating for the past generation, raising (good) but compressing (boring) the fortunes of the clever and the dimwitted alike.😉

Since realized volatility is sensitive to how we sample it, it’s worth looking a bit closer to how it accumulates. This exploration is likely to inspire your own research or even guide your thinking on how to get your head around return behavior that, despite being common and familiar, remains, as my kids say, confuzzling.

In this post:

  • The Trend Ratio — what the ratio of weekly-sampled to daily-sampled vol tells you about trending vs choppy regimes
  • The Variance Contribution Ratio — a single number that tells you whether a trend was a slow grind or a one-day event
  • Broad patterns across 35 liquid ETFs over a decade (~97K observations)
  • What TR implies for delta hedging — the tradeoff between rebalancing noise and sampling bias
  • What happens to forward vol after grinding trends, and what that means for pricing
  • A self-contained Jupyter notebook that fetches from yfinance and reproduces everything

 

the shape of volatility

EWY had a grinding rally. You can describe this as momentum, autocorrelation, trend. These are all ways to say the stock went on a quite a run. These descriptions mask something even more fundamental that we should make explicit. The notability of this run, even before describing its steady behavior, is that it was volatile.

Even if it’s 1% per day for 20 days this is volatile in the sense that the movement in the stock was unusual. We do not expect EWY to find itself over 20% away from where it was a month ago. Plain and simple. If we tallied all monthly returns, a move of that size would stand out as an outlier.

If a dog is wearing a dress, we would acknowledge that unusual observation before describing the color or material of the garment. Similarly, before describing the shape EWY’s move, we take it in, “That’s pretty remarkable.” You’d need to have a narrow definition of volatility, a definition that is divorced from an honest view of reality, to think otherwise.

It’s settled then, EWY was volatile. Great. Now we can think about the shape of the volatility. I’m going to introduce 2 measures that we can use in conjunction to classify volatile moves.

Trend Ratio

A common way to compute a realized vol for say 20 trading days is to average the sum of squared daily returns, take the square root, then annualize by √251. We’ll call this 20d RV sampled daily or 20d_RV for short.

Now compute the same realized vol but sample weekly instead of daily. The method is the same except for 2 variables:

  • 5-day returns instead of daily returns. Note that means only 4 data points, not 20.
  • Since you sampled every 5 days, you annualize by √251/20

We will call this 20d RV sampled weekly or 20d_RV_w

The ratio of weekly-to-daily vol captures how much “trend” was present relative to chop. We can call this Trend Ratio (TR).

TR = 20d_RV_w / 20d_RV

When TR > 1, the market has been trending. The point-to-point displacement exceeds what you’d expect from the daily noise. When TR < 1, daily returns have been partially canceling or mean-reverting within the window.

As of the last day of February 2026:

EWY

20d_RV_w = 49.9%

20d_RV = 40.6%

TR = 1.23

Variance Contribution Ratio

Imagine 2 stocks.

Stock A: Moves 1% every day. Its vol annualizes to 16% if you sample daily

Stock B: Moves .60% 19 days, and 3.6277% on 1 day. Its vol also annualizes to 16% sampled daily

Both A and B accumulated the same amount of variance, but for A, each day contributed 1/20 of the variance. Stock B’s most volatile day contributed 65.8% of the total variance!

💡Variance is the square of returns. We care about variance because realized p/l in options is proportional to variance. If you are short gamma, a 6% move costs you more than 2x a 3% move.

We will define a Variance Contribution Ratio (VCR) as the fraction of total variance explained by the single largest squared daily return. Hence, the VCR for a 20d window:

VCR20 = max(r²) / Σ(r²)

If all 20 days contributed equally to variance, VCR would be 1/20 = 5%.

Snooping ahead for a moment, the median VCR across 35 liquid ETFs for the past decade is about 25%. This means one day typically explains a quarter of the whole month’s variance. A major departure from the uniform case. The real world is lumpy.

 

Boiling vs jumpy frogs

A high TR reading tells you the market trended, but not necessarily how. By filtering TRs by VCR or vice versa, we can distinguish grinding or frog-boiling trends versus a trend characterized by larger jumps. From there, we can study subsequent realized volatility behavior.

I grabbed 10 years of daily return data for 35 ETFs spanning equities, fixed income, fx, and commodities from yfinance (~97,000 observations)

The details of all the calcs and code are in this notebook:

🔗https://github.com/Kris-SF/public_projects/blob/main/vol_ratio_vcr_study1.ipynb

Here’s a high-level summary:

Across all tickers, we can see that the median trend ratio is ~95%. In other words, volatility sampled weekly is about 5% less than if you sample daily. More frequent sampling over the same time window generally leads to higher vol computations, so this is not a surprising result.

If VRPs are typically 10-15%, then VRPs are about 1/2 to 1/3 larger if you sample weekly. An interesting observation for someone debating how often to hedge. The trade-off, of course, is noise. We can see the distribution of trend ratios in the blue histogram. Again, that’s across all tickers. For individual tickers, you can look up the standard deviation of the Trend Ratio. We will look at them graphically below in a bit. The distribution of TR appears well-balanced.

On the other hand, we can see that VCRs have a strong positive skew. The median VCR is ~25%, meaning it’s normal for 1 out of 20 days to comprise 25% of the total variance! It’s never the case that the distribution is truly uniform, but there’s about a 1 in 20 chance that a single day can comprise 50% of the variance. Remember, there are no single stocks in this universe, so earnings are not a factor. If interested, you could change the tickers in the notebook to study single stocks.

What’s normal at the ticker level?

Trend Ratios by ticker:

Commodities seem to exhibit more trending behavior than equities, but the overall feels compact with a range of TRs from .9 to 1

VCRs by ticker:

It seems like SLV and FXY have had about 10 to 20% higher VCRs than the typical name suggesting they are more prone to a single jumpy move in their return stream. Because we are looking at the median VCR I don’t think the recent SLV chaos is skewing the data. If I exclude SLV data from June 2025 until now, the median VCR only drops from 29.5% to 29.4%.

 

Classification

Split TR and VCR at their medians to get a blunt classification framework:

Summary:

Grinding Trend: 20,744 (21.3%)
Spike Trend : 21,605 (22.1%)
Choppy Grind : 28,046 (28.8%)
Spike Revert : 27,150 (27.8%)
TOTAL : 97,545

EWY’s move was textbook upper-left quadrant grinding trend. High TR, low VCR.

Let’s set VCR aside for a moment. It’s nice that the recent VCR confirms that the variance was not especially lumpy, but we can see that with our eyes. The question that prompted this whole post was whether the elevated TR, the fact that the less frequently sampled vol was much higher than the daily vol, meant anything for future volatility? Is the high IV actually expensive, or does the option’s market somehow balance both measures of realized vol?

Phrased generally:

Does the elevated TR tell you anything about subsequent realized vol?

For every observation, I computed both the current TR and VCR, then looked at what happened to daily realized vol over the next 20 trading days. To be clear, this is the window that is 20 days hence, so there are no overlapping days between the TR reading and the subsequent volatility.

I’m specifically interested if daily sampled vol exhibits any tendencies. I sorted all observations into TR quintiles and measured the median percent change (technically the log change) in RV20d from the current window to the next window.

The pattern is monotonic and the direction of change is what I’d expect.

In Q1 (lowest TR, most choppy) forward daily RV declines. To be fair, I had no expectation about whether it would increase or decline, merely that as we increase the TR, the subsequent RV would increase.

[To articulate the logic: there’s additional information in the less frequently sampled vol at the margin, perhaps uncovered by splitting the data into quintiles. We are looking for benefit in the margins as we accept that there is less total information than more frequently sampled vol. After all, daily vol sample would converge to a good estimate of an asset’s true vol faster than once a year observations. This is also why you would prefer daily data about a trading strategy versus monthly.]

As we ascend quintiles, Q5 (highest TR, most trending) precedes a median increase of +3.4% in RV20d.

The daily estimator was understating the expectation of the next period’s vol if we assume it would be unchanged. The next period, daily RV partially “catches” up.

3.4% isn’t a huge number, but it’s material. If you thought 50% vol is fair, now you might pad that to 51.7% but…it’s highly variable and positively skewed. The mean vol increase is 14.9%, which would mean raising your fair vol from 50% to 57.5%!

This is the histogram of the percent vol increase in the subsequent period for the 5th quintile of trend ratio:

Be careful, the standard deviation of that vol change is huge. This is all the quintiles:

 

That EWY elevated IV over daily-sampled RV starts making a lot more sense because its trend ratio of 1.23 is in its top quintile.

 

VCR adds independent information

High VCR predicts vol decline, holding TR constant. This is partly mechanical. To take an extreme example, when one day accounts for half your variance budget, vol drops when it rolls out of the next window. But it’s also real: spike regimes tend to cluster and then subside.

To examine how VCR may interact with TR, we construct a heatmap. Each cell shows the median percent change in daily RV from the current 20-day window to the next, broken out by TR (columns) and VCR (rows).

Reading left to right (TR axis): Higher TR predicts vol increase, and this holds within nearly every VCR row. Look at the 15-20 VCR row: it goes from roughly flat at low TR to +11% at high TR. The pattern repeats row by row.

Reading top to bottom (VCR axis): High VCR predicts vol decline across every TR bin. The bottom row (VCR > 50) is negative across the board, ranging from -30% to -3%.

We would find EWY in the upper right corner (high TR, low VCR) the grinding trend zone. Subsequent vol rises from +8 to +12%.

Recall from the four quadrants that grinding trend is the least common, showing up about 21% of the time. But this is still frequent enough that you can easily bid an IV equivalent to the trailing daily-sampled vol.

I just doubt that the market will give it to you. But at least you know to screen for this and at the very least not be tricked into selling an insufficiently high IV.

It’s trivial to compute a VCR as well, so you can add this filter as confirmation that the trend is boiling a frog not just a jump.

The Notebook

Again, I’ve open-sourced the full Jupyter notebook behind this analysis.

🔗https://github.com/Kris-SF/public_projects/blob/main/vol_ratio_vcr_study1.ipynb

It fetches data directly from Yahoo Finance, constructs all the variables from scratch, and reproduces every chart above. You can change the ticker universe, the window length, or the sampling frequency and re-run the whole thing.

Note the code computes TR and VCR using a zero-mean estimator for realized vol (dividing by N, not N-1). This is deliberate, we’re measuring total quadratic variation including drift so the zero-mean formulation is standard in the vol trading world

hard earned trading wisdom

Euan Sinclair needs no introduction from me.

I’ll cut straight to the gold.

He’s been a repeat guest on Erik’s Outlier Trading podcast a few times. His writing and interviews mince no words. Despite never sugar-coating the reality of trading, I found his most recent interview even bolder. It’s this witch’s brew of insight that is somehow both timeless and underreported.

I’ll start with an idea from the interview he did from late 2025 that always bears repeating before moving to the more recent chat.

The most common misconception about trading volatility

In Euan’s 2025 chat with Erik, he was asked “What is the most common misconception about trading volatility?”

He zoomed in on the mistaken logic that because volatility is mean-reverting, selling it when it’s high assures a profit since it always comes back down.

There are several facets to the mistake. One is with respect to how volatility can cluster based on a market regime.

Saying volatility’s mean reverting is true, but the means also change, you know? So, if you sold volatility in, I don’t know, March 2020, right? Volatility didn’t go back to 15 for about a year, right? Volatility had a new normal. So just because something’s mean reverting doesn’t mean you’ll make money because it comes back.

Another flaw is in understanding that you are exposed to both realized and implied vol.

The other thing that can be wrong is that you’re not directly trading volatility. You’re trading the spread between implied and realized. And that doesn’t have to be mean-reverting and it doesn’t have to be negatively correlated with the level of volatility either. So just because the implied V comes down, that’s not necessarily going to help you if the realized vol still is higher than the implied.

[Kris: I remember suffering through a short option position in nat gas in the expiry right before I got married. The V09 option cycle (expiry date was late Sep 2009). Implied vol got up to 110% but it realized more than implied for our entire holding period. We chopped ourselves up on the short gamma even though we had “positive vega p/l” on some of the marks.]

It’s easier to understand this when you scrap the concept of “vol” for a moment:

Forget about volatility, right? Volatility is just a way of turning option prices into another thing. It relies on a model. Forget about all that, right? Let’s say you’ve got a straddle and the straddle’s trading at five bucks and that straddle normally is trading at two bucks. So you’re like, “Oh, that’s really high. I’ll sell it.” And then as soon as you sell it, it moves by $10. You know, the stock moves by 10 bucks. You’ve just got hammered, right? But you know, the straddle drops down to a dollar. So you were right about the price of the straddle, but you weren’t really just trading that.

Finally the VIX chart illusion:

That’s one of the problems people get wrong is selling volatility spikes isn’t as appealing as it looks as when you look at the VIX graph over time and you’re like, “Oh, the VIX these spikes. It always comes down again.” Yeah, but you that’s not what you’re trading when you’re trading options.

See this post from the Liberation Day period if this is not clear: you can’t trade spot VIX.


The rest of these excerpts are from Euan’s 4/1/26 appearance on Outlier. Emphasis mine.

Where to start: known effects

Erik asked Euan where retail traders should start. Euan’s answer is a tour through what he actually believes works, why it works, and how to think about learning from past data without fooling yourself.

If you’re prepared to have low enough expectations that they’re realistic, and then really work at this, um, and it doesn’t have to be a full-time job, but you can’t just think this is my extra income. You know, this isn’t like driving for Uber.

Erik: Thinking a little more deeply then about the kind of things retail traders should look at — I went through an interesting exercise on my own, because people would ask me for ideas on places they might want to start looking, and I always struggled to give a good answer. There’s a million variables. But I’ve recently started directing people toward really well-known market effects — stuff you could go look at research papers on SSRN in mass, well-researched stuff. Something like time-series or cross-sectional momentum as a general market effect.

The reason I’ve been going that route is that there are so many things you have to do right as a retail trader. Even if you’re doing all the right things but it’s centered on an effect that isn’t really there but you think it is, that’s massively detrimental long term. Even though the returns might not be — as you talk about — stuff that would give you Lambo money this week, you’re at least building the infrastructure around something we know exists.

Are there effects or markets that you think are better suited for those first few repetitions for a trader?

Euan: It’s not so much about finding a market where you have an edge. It’s not like, “Oh, you’ve got to trade shitcoins,” or “You’ve got to trade options on pharmaceuticals.” The actual instrument and sector are of lesser importance than the concept of what makes this thing work.

There are a few things in finance that we know broadly are real. Momentum is one. The other one I’d say, if you’re just starting out and you want to set up what I’d call a real trading operation, would be carry.

If you really understand the concept of carry, particularly as it applies to futures basis trading — in theory, we know that a future is going to coalesce to the spot price at expiration. But that doesn’t tell you how it’s going to do it. It doesn’t say the future’s going to stay there and the spot’s going to go up toward it. It doesn’t say the other way around. But what actually happens most of the time is that the future moves toward the spot price. Naively, that’s exactly what you wouldn’t think happens — you’d think the future was an expectation of the future or whatever. But no. It doesn’t matter what you naively think. That’s a very strong effect.

If you know about that effect, you’ve now got lots of places you can look for ways to apply it. And if you understand the effect, you’ll know places that are better than others. You look for something with a big basis. You look for something with high volatility, because that also gives you more of a basis. And you want something to move a lot, because if nothing moves, you can’t make any money.

That leads you to something like the VIX. The VIX futures have a very high basis to the cash usually. If you look at the difference and you annualize it, if that entire basis is realized, that can be 100% a year. Are you going to get 100% a year? No, because lots of other things are going to happen, and you’re not going to realize all of that, and there’s volatility. But that’s now an effect where you can start saying, “Okay, now I know this. What can I do to harvest it?”

Then you start saying, “Well, clearly I want to be short the future if it’s above the cash. That’s risky. What do I do to hedge that risk until I’m happy?” And maybe you’re like, “Okay, I’ll do a future spread. I’ll be short the front one, long the back one. What ratio? What futures?” Eventually you’re going to come up with — and there are papers written on this exact effect, I haven’t just pulled this one out of nothing.

A lot of the stuff’s out there. People tend to have this idea that no one’s going to tell you anything that works, whereas literally there are thousands of pages written on stuff that works. The universe isn’t going to give you money the way you want it to necessarily, but this carry effect — once you understand it in the VIX, then you’re like, “Holy shit, this also works on a ton of other commodities. It works in bonds.” And then, “Okay, if it works in bonds, does it work differently in treasuries, credit, corporate bonds?” And the answer is yes. So now you’ve got spreads. So relative value is the next thing you start looking at.

Pick a bunch of carry situations, learn to put them on, learn to manage them. They largely take care of themselves, but you have to adjust, you have to understand the risks. It’s like when you fly a plane — you’re learning on a Cessna, learning slowly. You don’t just get into a MiG and blast off. But this is that Cessna. It’ll get you money, and it’s a real trading operation.

Then you move on to relative value. These spreads move around. Maybe I can scalp those spreads. How do they move around? What’s the range? And then, “Well, sometimes they don’t move around.” Okay, and that’s going to lead you to momentum. That’s your next one.

Everyone should read that book by Antti Ilmanen, Expected Returns. It breaks down — it’s about 400 pages long, that’s how detailed it is — and it talks about the volatility premium for about four pages. It goes into hundreds of things like this that work. Carry is a huge unifying feature. Relative value. Momentum. The variance premium and options — again, that’s there. I wouldn’t recommend people start with it. It’s kind of slippery and a good way to lose a ton of money unless you’ve got everything else sorted out. But it’s another one.

That’s where I’d start. I’d start with one thing, move to the next, keep adding. Once you got to three or four things, that’s probably all you can handle. You’re not going to be able to have 10 different strategies and keep things together. That becomes a major logistical operations issue.

Where to expect edge: the hard leg is where the money is

[Kris: My biz partner would say the “hard leg” is where the money is.]

Typically in the world, you get paid for doing something that makes the world somehow better. You provide a service, and typically there’s something unpleasant about that. Otherwise people will just do it themselves.

If you’re selling flood insurance, that’s a tough business because you make money, make money, make money, and then you get absolutely blitzed. That’s a tough thing to live through. Everyone thinks they can, but in reality it’s a lot harder than you think. We’re very bad at figuring out how we’ll feel when something bad happens. Similarly, the guy in the flood who’s cleaning out the sewers, he gets paid.

If you’ve got a clear idea of, say, the carry trade — why am I getting paid to do the carry trade? Largely because I’m providing a source of risk insurance for other people. I’m short those futures that are going to go massively up when the market — like a couple of weeks ago — when the VIX spikes from 18 to 30, those short front-month futures are going to hurt you way more than the long back months. And they have to. Because if you hedged that, then there’s not going to be any premium for you to take out of the trade. All of these things are risk premia. In order to get risk premia, you have to accept that risk. Over time you’ll be fine, but you’ve got that unpleasant nature of the payoff.

Another good rule of thumb: anything where you think this is a bad idea because the risk looks unpalatable — there’s probably edge in there somewhere. If you as a professional trader are like, “Yeah, this looks dangerous,” you’ve got to accept that most of the rest of the world also thinks it looks dangerous, and you get paid to manage that fear. You are the bomb disposal guy. That’s why you’re getting paid.

So if it’s like, “Ooh, there’s no way I’d sell options over the weekend, that’s dangerous” — all right, what side do you think the edge is on? The guy who is prepared to sell options over the weekend, or the guy who wants to buy options over the weekend?

Walking into danger — I’m not saying you always have to, and it’s a risk judgment; you don’t have to take every risk that’s out there. But if it makes you nervous, there’s probably edge in there somewhere. If you can get it to a point where you’re comfortable with it, or can diversify, manage, or hedge it, that’s a good place to start making money. That’s why you get paid for selling options. You don’t get paid for buying options.

Again, difficult thing to say, because for the last three or four years, retail made a ton of money buying 20-delta calls in the indices. By the way, historically, what’s the worst option to be long? Index 20-delta calls. If you think that’s your edge — no. Take that money and good for you. But that’s not the way the world has typically worked. It might work like that for the rest of my life, who knows. You’ve got three years where that worked really well, and 100 years where it didn’t. Just as long as you know that.

Look for any situation that legitimately makes you uncomfortable, and there’s probably something in there.

Learning from the past

Erik: Two follow-ons. I’ll give you both, and you can pick. The first is how to use past information to inform future projections or predictions. The second is pricing of convexity and some of the internals behind that. You pick whichever one sings to you.

Euan: I think the first one is probably more suited for a podcast format.

Basically, the only thing we have to predict the future is the past. And there are two things you can say: the future will be somewhat like the past, or it won’t be like the past. Of those, clearly the better one is to say it will be somewhat like the past. That just makes sense, and usually that’s the way it’s been.

The problem, particularly in finance, is it’s an adaptive system with people on the other side of, and everyone is going through this thought process to a certain degree as well. Everyone’s looking at the same information. Everyone’s saying, “This is the way it’s behaved.” Everyone’s trying to predict on the same thing. Largely coming to a spread, but broadly the same conclusions.

So using the past to predict the future is always going to be murky. And there’s an unfortunate tendency we have now. Like, 30 years ago, no one did backtesting, because you couldn’t. There was no data, no computers. Even before Excel — you’d have to write a program in Fortran. It was hard. No one did it.

Now, everyone does backtesting. The problem is that means most people do it wrong. They see backtesting as a way to find patterns, and they’ll test stuff, do cross-validation, test walk-forward, go out of sample, and they’ll find things. The problem is they look at so many things. Of course they’re going to find something. That’s the big problem with using the past — you think you’re doing statistics correctly, but really all you’re doing is looking at stuff over and over again until you find it.

You’ve also got to remember — and this is an Aaron Brown thing as well — as soon as you’ve looked at some data once, you’re done. That data is in sample forever. You can’t say, “Oh, I’ll try my trend-following system on the S&P. That didn’t work. I’ll try a mean-reversion system on the S&P.” The only reason you’re trying that mean-reversion system and think it might work is because your trend-following one didn’t. So you’re already overfitting. It’s not so much overfitting to the numbers. It’s applying information you’ve learned by looking at it already, even if you’ve looked at it for a different thing.

At this point, there is practically nothing I can do to study the VIX that’s going to tell me anything, because I’ve looked at the VIX for so long that I know what’s in there already. I’m not actually making any sort of new judgment. All I’m doing is applying what I know has worked in the past because I’ve looked at it so many times.

The way to address that is to start with something you believe first. Do you believe in carry? Yes. Do you believe in momentum? Yes. Cross-sectional momentum? Yes. Risk premia? Yes. And then you come up with an idea, and then you say, “Does this work in the past?” And you test it. If it works, great, you can make it better. If it doesn’t, you give up.

We see this with options particularly. People are like, “Well, I tried selling strangles on Monday and holding them all week and it didn’t work. But then I found if I sold straddles on Tuesday and got out on Thursday, it did work.” Both of those are driven by the same effect — they’re both variance premium plays. If one of them didn’t work and the other one did work, all it means is you got lucky picking the entry point for one and not the other. As soon as you’ve looked at that second one, you’ve just completely overfit the whole thing.

That’s one of the big problems people make by using past data. You use past data to come up with the overall belief. Carry means something. Credit spreads mean something. We’ve got, I don’t know, 5,000 years of stories about credit. Credit’s older than money. It’s a real thing.

Looking at numbers should be the last thing you do, and only to confirm something you’re already pretty sure works. My risk premia thing — I’m sure it works. I can test does it work better in a one-month option or a one-year option, but I should not be just blasting combinations in until I find something that is the best.

One of the most dangerous words that’s come out in quant finance is certainly “alpha drift.” This isn’t a retail problem either. I see this in quant firms all the time. They optimize and think they’re doing it out of sample, but they’re not, because they’ve already — this is the fourth model they’ve run on the same data because they keep looking at the S&P 500 or something.

Optimization is a horrific thing. It’s one of the worst things to ever hit the world of finance — that concept that you can make something better, or perfect, or optimal.

The other one, by the way, is theta. I can’t think of a thing that’s cost any more money than theta — this idea that options decay over time. That is literally not what the Black-Scholes equation is telling you. The Black-Scholes equation is literally telling you they don’t. If everyone knew an option was decaying over time, no one’s going to pay for it now — they’ll buy it tomorrow, it’ll be worth less. The number of people who’ve fallen into that “I’m harvesting theta” thing — and there’s plenty of influencer types who are peddling that story, typically also owning a brokerage at the same time.

The difficulty of learning from the past is that people think they can learn too much from the past. You have to discount everything you know based on how much you actually believe the thing. Show me an effect you found in the market — I don’t know what it is. A few years ago, “gold goes up on Fridays” was a big thing. Everyone looked at the data — look, gold went up on Fridays. Okay, why would that happen? “Well, it’s because fund managers are scared of risk and they go into gold on Fridays.” All right, find me one of those people. Not you, or some other person who buys gold on Fridays. I mean someone who runs an appreciable amount of money — doesn’t have to be Pimco, but people who run hundreds of millions or billions. Show me one of those people. No one’s ever managed to do that.

Does it go up on Fridays? Well, it looked like it did. T-stats, sure it did. Now how much do you actually trust that? On a scale of zero, which is candlestick charts, to 10, which is carry is a real thing — I’ll give gold on Fridays a three. Could it be true? Sure. But I don’t see a compelling reason. You look at enough things, you’re going to find that.

That’s the problem people get. They look at the t-stats and go, “Look, statistics, man.” All right — now how many other things have you looked at that didn’t work? Because you’ve got to include those.

The philosophical problem of what you can learn from testing

Starts with sound reasoning:

I’d like to start with the idea that people buy bonds at the end of the month because of window dressing and rebalancing of 60/40 funds. There’s an idea. If the stocks go up more than bonds in a given month, people rebalancing have to sell the stocks and buy the bonds. That should have an effect. That’s your hypothesis.

So let’s look for situations where that hypothesis has a market effect. Do you see it? Do you see it in situations where your hypothesis would tell you you should see it? Equally, do you not see it in situations where your hypothesis tells you you should not see it? If this also happens on the second week of the month, maybe it’s not what you think it is.

I’d always like to start with a reason and then test the reason.

…But there’s thousands of years of philosophers who pointed out all the contradictions in this stuff. Nothing in the world is out of sample. The only person in the world who’s out of sample is a baby who doesn’t know anything. That’s the great curse — the more you know. With me and the VIX, it’s not that I’m the greatest VIX person in the world or even close. I’ve just looked at it, I know it, I can’t be surprised by anything it does. That’s the downside of experience: nothing is out of sample…

The best you can do is find a situation that looks like it’s somewhat constant over time. If you look at the statistics of the VIX, the distribution is pretty constant. If you look at what it did in the ‘90s and in the 2000s, break it down in big blocks — it kind of looks the same. Whereas stocks tend not to. You can’t look at Tesla 10 years ago and Tesla two years ago. The business models were totally different, but in one case the stock was a dollar, and over the last two years it’s been between 200 and 400. These are different situations. Stocks are not stationary.

But really, one of the things you have to do is accept how little you know about the world. The good traders never say, “I’m right because of this, and this, and this.” The good traders are like, “I think I might be right because of this. But on the other hand, I could be wrong because of this and this and this.”

Aaron Brown, who’s probably thought more about this stuff than anyone I know, says that a bad trader is always saying “and furthermore,” and a good trader is saying “on the other hand.” A good trader is looking for holes in their argument. A bad trader is continually trying to find other reasons why they’re right.

David Hume — smart guy, all philosophers do is think about thinking — they were pointing out the problems of trying to learn from induction hundreds of years ago. There’s no answer. That’s the only information we have, but we can never really draw certain conclusions from it. So I always apply a big whacking discount to everything. And it’s not statistics. It’s a meta level above that. It’s like belief. I’m not just saying there’s a statistical rule for how you judge if this is good or bad. In fact, literally there isn’t. There’s an actual degree of belief that is independent from what the numbers are telling you.

Vibes vs quant is a false dichotomy — there’s vibes in everything

[The general construction of his portfolio isn’t] based on statistics. It’s based entirely on my degree of belief. Like that carry trade we talked about — how much do I believe that? A lot. Given what I know about its volatility — and I mean “things move around” volatility, not standard deviation of returns — given I know how much that is, given I know how scary it can be, but given I know the belief, I might give that 40%. Whereas there might be another trade where statistics are just as good, but I’m like, I don’t know, I don’t really believe in that one. That gets 20%.

That gives me my baseline, and then I go run all the statistics, and then I say, “Well, okay, I’m shrinking it to this vibes portfolio, because that’s the one I kind of wanted to be at in the first place.” There’s a lot of people who’d be like, “Well, that’s not quantitative. That’s not systematic.” Well, first of all, who gives a shit what they say? You don’t get a medal for being quantitative. You make money or you don’t. Being quantitative is seen as this kind of goal, and it’s not the goal. It’s a tool toward the goal.

Every time you make a portfolio or sizing decision, you are at some point applying that kind of thing. If you’re going to go through all the math, eventually you’re going to have a utility function, and that utility function is going to have a risk aversion parameter. So you’re going to go through all this math, and then at the end it’s going to say, “Oh by the way, what’s your risk aversion parameter?” You have to make that decision somewhere. I’m just doing it at the start. It’s much more of an exogenous thing that’s obvious.

It’s more a reflection of what I think I actually know than a mathematical statement. It’s not a mathematical statement. It’s an epistemological statement.

A lot of people get hung up on “insult found: the discretionary trader.” How is that an insult? Everything you do is discretionary at some level. Literally, you have chosen to do something. You have exercised your discretion to do something. Whether you do that in the math you choose, the problem you attack — you can’t go through life without exercising discretion. That’s actually called knowledge or experience. It’s a useful thing. If you don’t use that, you’re an idiot.

The cost of systematization

There’s certainly this whole idea that if you’re systematized, it’s emotionally easier to stay with things. I don’t think that’s true. I have operated completely systematic stuff when I’ve had jobs, and it loses money. It’s not easier. It just isn’t.

The reason I think you should systematize something is because you have to. Every time you’re removing yourself from interacting with the market, you’re removing yourself from an opportunity to learn. I think you should do things as manually as possible — and I mean it. If you can get away with writing stuff down on a legal pad, then that’s the way to go. If you need to use a spreadsheet, use a spreadsheet. But if you can do it on a spreadsheet, yet you choose to write some massive API call and do the whole thing in some language — you’ve done that because you wanted to, not because you needed to. That’s a mistake.

The places I’ve systematized things are because I wanted to avoid operational risk and key-man risk. If I’ve got a strategy I want to run for an ETF every day, it has to operate if I crash my car and go into a coma. That has to be systematized. But if I’m running something on my PA because I find it interesting and I’m still messing around with it — systematizing that, all I’m doing is removing the opportunity to learn.

It’s one of those things where retail look at institutional and go, “Well, it’s all systematized. I have to do that.” But they don’t think of the reason we systematize things. It’s not to make the strategy better. Honestly, it probably makes it worse, because you’ve locked it in. You’ve said, “This is it, I’m not going to be learning anything more about that now.” But it definitely removes operational risk. It makes it cheaper to run, because you can just let it run on its own. You don’t need a person doing it all the time.

People on the outside are making a judgment of how the things on the inside work, and they’re missing the point.

How do you avoid it? I don’t know. Hopefully if I pointed that out to you now, you’d be like, “Oh yeah, now I get it, this is the important thing.” Think about anything else you’ve ever learned. You’ve learned by doing, by the immersion in it. Trading now, the actual act of trading, is click, click, click, done. You don’t learn anything from that.

But what you do learn about — especially things like adverse selection and the ability to execute — like, “Oh, it looks like there’s plenty of volume. Oh, but every time I put a 100 lot in, all the bids disappear.” That’s the sort of thing you’ll learn so much about just doing it and interacting with it. You’ll never learn that if you automate the trades.

[Kris: To insert something here. I’m reminded by an interview with Agustin Lebron where he talks about getting ideas from just staring at an order book for ours. Seeing how it updates, how bids and offers change after trades, or in the absence of trades but while the rest of the market is doing things. He recommends doing this in medium or low-liquidity names where you can possibly see a story unfold in the order book. I agree with all of this. I mean I don’t think I never explained it quite like that because it’s just the water you swim in. If you trade something relatively illiquid, every movement matters. If some 20 delta put trades on the offer, you have to triangulate whether it’s skew expanding or volatility in general. See Mermaids, Fireflies, and the Bid-Ask Spread.

But there’s a corollary hidden in wisdom of learning from sparse order books: edge is inversely related to liquidity. The more liquid the market, the more whatever’s left looks like a risk premium. SPY is one of the most liquid markets in the world. If you had any edge in trading it, the edge would be so scalable your heirs would be set for an eon. Remind me to rant about this sometime.]

If you’re in a situation where you have to automate the trades, you’re probably playing in a game where you’re not going to win as a retail trader. You shouldn’t be trading, “Oh, I have to run this through the API so I can trade 15 times a day.” That’s one of those quant-envy things where you’re like, “I’m going to do this the way Citadel would do it.” Again, you’re playing basketball one-on-one with LeBron. Good luck. Don’t care how tall you are.

Inefficiency vs risk premia

There’s a split between inefficiencies and risk premia. With an inefficiency, price competition is going to drive it to zero. Nothing’s purely risk and nothing’s purely inefficiency, but market making in options has a lot of inefficiencies. It’s like, “I’m going to buy this option because I can sell this option. Those things should be worth the same. They’re off by a little bit.” That kind of thing. The act of providing liquidity is a risk premium, but the way you do it is looking at all these little inefficiencies.

If you look at the way equity market making has gone in the last 30 years or whatever, ever since the floors have gone and we’ve gone electronic, that has been driven to almost zero. It’s not at the point now where any sort of random person with an off-the-shelf piece of software is going to consistently make money making markets in equity options anymore. It’s gone from profit margins like Tiffany’s might have, and now it’s Walmart. Everything’s driven to zero.

Risk premia are different, though, because they’re there for legitimately a reason. It’s a different utility function. You’re doing something you know is wrong because you don’t want to deal with the risk. You’re buying insurance. You’re not buying insurance because you’re dumb, you’re buying insurance because you want insurance. And I’m selling it to you because either I can take the risk, or I can lay off the risk, or whatever reason — I’m doing it to maximize expected value. You’re doing it to maximize another utility function. We’re both happy.

That kind of thing has got more legs to it. If you look at the variance premium over time it’s been reasonably constant. Obviously it goes up and down. You’d think that after 2008 it would get wider; surprisingly, didn’t much. You’d also think that now, because of all these zero-DTE covered call funds, it would collapse. And it kind of has. But sooner or later people will realize a lot of these funds don’t make money, or some of them will blow up, and it will go back to where it was. All these risk premia are cyclical, but there seems to be a natural limit that doesn’t get driven to zero.

It helps to be able to say: is this an inefficiency that people can’t access, or is it genuinely a thing that everyone knows is there and people are doing it for different reasons? Because that’s the sort of thing you can build a trading life around. Inefficiency — if you find one, good for you, knock it out of the park as hard as you can. It’s not going to be there forever. If it is there forever, Citadel is going to come along and build a desk on it and crush you.

Adaptive markets, but not adaptive traders

Erik: The follow-on, though, even within something like risk premia that we know is there for a reason — an example you’ve given previously is there’s a $20 bill on a busy highway. If I’m standing on the sidewalk and there are five crackheads, and I say, “Hey, I’ll give you 10 bucks to go get that.” And then one of the other crackheads says, “I’ll do it for eight. I’ll do it for five.” And then at some point we get to a floor where the crackheads are like, “I am not going to risk my life for this anymore.” Do you think that with something like risk premia in index options, based on that consistency, we’re generally about at that level? Or do you think it’s likely to shift around more?

Euan: That’s difficult to say. But with your crackhead example — one crackhead might say, “I’ll do it for six bucks,” and he runs out there and he gets killed. And then the next crackhead’s going to come along and say, “Actually, I want seven now, because I saw what happened to this guy.” It’s not the same people all the time.

What we tend to see is a new cohort of traders come in and blow up doing the wrong thing, and then a bunch of other people come in and end up doing the same wrong thing. The market never completely adapts, because it’s never exactly the same group of people who learn. Markets learn, but traders as a whole don’t. For things like this, a lot of it’s propped up by new people coming along making the same mistakes as the old people. Adaptive markets, but not adaptive traders. In a lot of cases people think they’re the same thing. I don’t think they are. There were a ton of floor traders, good floor traders, and then everything went electronic, and they tried to do what they did on the floor on the screen. It just didn’t work. And I don’t know any of those guys who were like, “It’s not working, I’ve got to do this and this and this instead.” That didn’t happen. Instead, a whole bunch of other people — studied computer science at Cornell or whatever — came in. It was a whole different group of people who made money at that point.

options policework

A moontower user sent this [paraphrased] message in our Discord the morning of Jan 9th:

NLR [VanEck Uranium and Nuclear ETF] had a price shock on Jan 2 and has been ‘fast grinding up’ since then. Did I “lose” here because RV climbed up faster than RV and my losses are ‘gamma’ driven?

Now the most important part — what can I learn / what should I do as part of my process?

We are going to do the post-mortem in steps. The first task is to take inventory of the scene. Basic policework. “What happened?”

Once that’s established, we can at least start to disentangle bad luck from decision quality and finally wrap up with risk management/hedging/whether we should close the position or not.

Arriving at the scene of the crime

What do we know? Our friend sold a small amount of 1-month NLR at-the-money straddles in December. To be discreet, I’m going to guess the date to be December 15th and the strike to be the 126 line and IV was ~41%

Below is a simple time series of:

constant maturity 30d IV LAGGED vs 30d realized vol

By lagging IV, we align it with the 30-day realized vol that was experienced in the subsequent month. We can see that the RV (faint green line) our friend experienced far exceeded the IV (dark blue line) of the straddle they sold.

A chart like that is a handy compression, but since it is:

  1. using constant maturity vols (ie interpolated) and
  2. floating (the IV is taken from the .50 delta call each day)

…the chart is not high-resolution to discuss p/l, but can only gesture roughly to its direction. It’s a blurry picture of a license plate as the driver speeds away.

We will get down to the contract level, but first, we want to develop a sense of proportion about notable move sizes.

Realized vol

Jan 2nd was the steepest one-day move: 7.1% or about 112% vol annualized. Nearly 3 standard devs.

 Over 8 days, there was a 13% cumulative rally, or 73% annualized vol.

The calculation: 13% *sqrt(251/8) = 73% annualized vol move

Any funny business under the hood?

  • NLR’s largest component, CCJ, is ~9% of the basket. It rallied a bit over 7% as well which is frankly underperforming the basket since CCJ is a higher vol than the ETF.
  • Its second largest component is DNN ~6% but lots of names in the basket are close to that size. DNN was up 14%…but its normally twice the vol of the ETF already.

In z-score space, the ETF and its 2 largest holdings all moved about the same amount.

All these clowns are riding in the same car. Its a 1-corr move, in a beginning-of-the-year inflow to this sector.

💡For those of you who trade around rebalancing and calendar anomalies, perhaps this is a thread to pull on?

Drilling down to the option contract level

The NLR option volume in the month preceding Jan 9th was not notable. There was a spike in puts traded on Jan 5th, but this was already after the largest single-day move happened

The largest component, CCJ, did not have any noteworthy volume in the prior month either.

What stands out in NLR is how small the open interest is in general. This is not a liquid option name.

Price and P/L

From December 15th to Jan 9th, the Jan 126 straddle expanded from $12.75 —> $15.50 as the stock went to $140. No surprise, the call went to >.90 delta.

So the short straddle position lost $2.75, assuming you did not hedge any of the delta on the way up.

If you’re intent is to trade vol, allowing the delta to ride like that is introducing a lot of noise into your trade expression that was supposed to be about vol.

What if you sold the straddle and hedged the negative gamma daily by bringing your deltas back to neutral? In other words, buying shares after they rallied and selling them as they fell in opposition to the changing straddle delta.

Our service includes an attribution visualizer which allows you to decompose your daily and cumulative p/l due to realized and implied vol changes as the option and stock price move around. It is from the perspective of an option buyer. In this case, we are selling, so just flip the signs. We also need to double the numbers since we are assuming a straddle hedged daily, not a single call or put as the tool assumes.

The total ACTUAL delta-hedged p/l as of January 8, the day before the friend messaged the group, would have been -$.51 per contract or -$1.02 for the straddle. The loss would have been less than letting the straddle ride, since the stock trended up and each rebalance would have forced the hedger to buy on the way up.

If the stock chopped around at 70 vol but still landed on the strike, hedging would have locked in a bunch of negative gamma scalps while the straddle decayed.

Hedging makes your p/l reflect the vol that was realized but whether this is good or bad for you, ex-post, depends on whether the stock chopped or trended.

Ex-ante, you want your hedging to be aligned with the reason for your trade, which in this case is presumably the expectation that IV would have a risk premium above realized, since the trade was selling 1-month atm straddles.

A note on attribution

The chart doesn’t track the sum of unexplained p/l although it is displayed in the summary (not shown). The “unexplained p/l” is the balancer which makes the theoretical attribution tie out with the actual p/l. It is a catch-all for the higher-order greeks, mostly vanna and volga, which reflect the fact that your gamma and vega, respectively, are not constant during a single day’s move.

The bulk of the p/l on that big day is due to realized. It’s fair to say from the summary that realized p/l explains most of the result. This is what we’d expect from an option with only a few weeks until expiry.

No smoking gun

Given the lack of notable action in the option volume in either NLR or its components, the uniform behavior of the moves in the complex, a boring IV chart to close out 2025, and the fact that the move happened on the first business day of the year, that this result was a bunch of methodical but unanticipated sector flow. Approximately 2.8 sigma move in one day, or about 1/200 probability, a bad beat with roughly the same probability of being dealt pocket aces (1/221 because 4/52 * 3/51).

[Stock moves are fat-tailed, so the probability is actually larger than 2.8 sigma would predict, but the fact pattern here still suggests a bad beat. The IV wasn’t suspiciously high in December, there wasn’t any telegraphing flow].

An opportune time to remember one of the reasons gambling and poker experience is helpful…from why poker is used to train traders:

This is one of the great teachings of poker. Short-term results are noise. He explains that in Limit Hold’em, even a high edge hand has only .02 big bets worth of expectancy vs a standard deviation of 2.5 bets.

[Kris: In investing language, a .008 Sharpe for one trial. The SP500 has a daily expectancy of about 3 bps and 100 bps standard deviation for a daily Sharpe of .03. The poker hand has almost 4x the noise of the daily SP500 return.]

Since poker teaches that you will make the right decision and still lose money, it trains you to emotionally decouple decision quality from result quality.

This is a ceaselessly profound concept. Not because it’s so clever, but because of how it resists internalization. It’s easy to understand, it’s hard to apply the understanding to how we receive the world.

As police work goes, there will be no verdict or even charges brought as to whether the decision to sell the straddle was sound. We do get research inspiration. Is sector dispersion especially high on the first of the year? First of the month? Is there more volatility in general on those days? If so, is the median volatility higher or the mean (ie is it being driven by outlier-type moves)? We don’t know if selling the straddle was bad, but we do get new questions. This is what a career in trading looks like. If you don’t like this type of problem, then hooray, I’ve saved you a bunch of time compounded over your life. You’re welcome.

Regardless of the outcome, we still have this business of risk management.

Should our friend have hedged or closed the trade?

We don’t get to snoop forward in time.

The following is true but unknowable in advance:

  • If the stock is trending, you want to hedge aggressively. Buy delta as it rallies, sell it as it falls.
  • If the stock is mean-reverting, you want to sit on your hands.

Your risk approach cannot depend on what you don’t know. And it must depend on what you consider tolerable.

The combination of these constraints will dictate how big your position can be. We’ll call this your limit. From there, you are simply monitoring how big your position is under various scenarios to that limit. If it is greater than the limit, you must reduce it.

I’ll give a simple example, but know this is a vast topic and a chief concern (and unsolved problem…there’s no single answer to this) of any risk-taking outfit.

Let’s say you are willing to tolerate 1% volatility in your total portfolio due to a particular trade on your average day. If you have a $1mm portfolio, that’s $10k. To a first approximation, that means keeping your swings due to delta below $10k. Call NLR a $140 stock with a 48% vol. For a typical day, that corresponds to 3% moves or $4.20.

$10k/4.2 is the daily swings associated with ~2,400 shares or 24 100 delta options. Or 48 50 delta options.

So what is NOT conservative about this risk-based sizing:

  1. “Typical day” is being proxied by 1 standard dev (ie the 3% daily vol). If moves are normally distributed, that means about 1/3 will be greater than that or more than a week out of every month will be composed of bigger moves. And that’s ignoring fat-tailedness
  2. We aren’t accounting for adverse vol changes. If you are short options, trades are negatively skewed so we’ll want to be more conservative still.

What IS conservative about this risk-based sizing:

  1. If you hedge your deltas even once a day, you will not have as much daily variance in your p/l due to delta, which is effectively what we’re describing above.

How does this shake out?

A good starting point!

In the case we’ve been following, if our friend used a rule like this, it woud have prescribed 48 50 delta options or 24 straddles.

The straddle went from $12.75 to $15.50 on a bad beat with no hedging.

The loss = 24 straddles * -$2.75 * 100 = -$6,600

If our friend hedged daily, mirroring the attribution visualizer recipe, the loss would have been:

The loss = 48 contracts * $-.51 * 100 = -$2,448

Notice the constraint:

This makes sure delta is positive for the sake of the calculation AND doesn’t allow you to oversize a position just because you chose a skinny option.

I came to this example from the perspective an option seller. If you are a buyer the most you can lose is your premium if you DON’T delta hedge. You can use your risk tolerance for losing money as your premium spend limit.

If you do delta hedge, you can lose many multiples of your premium. For example, if you buy an OTM put and the stock grinds down slowly to your strike, you will be buying shares all the way down. You will lose not only on your stock trades but also on the premium going to zero. T

I’m going to pause for a second to level with you because I do feel some almost paternal responsibility stemming from the privilege of many smart but also young readers who come to this letter to hear from me because of my gray hair and specifically because I won’t treat options like the next house-flipping get-rich trend.

This topic of risk is so vast that its discovery is an ongoing project throughout your career. You are shaping and being shaped by the rules you create and their feedback, so to think there’s an “answer” is to not appreciate how many facets there are to managing risk across a portfolio of non-linear instruments.

To recap…this was a “3 standard deviation” move and the loss was comfortably below our tolerance. You can season to taste, but this is overall a conservative approach that you can experiment with. This is a point-to-point p/l, so the rule is providing some flex for tough marks along the path. Like I said, a starting point.

🔗If interested, my treatise on hedging If You Make Money Every Day, You’re Not Maximizing

What the risk management decision is NOT about

Whether you should have the trade on in the first place is not the realm of risk management. That’s the alpha signal or whatever you want to call it in your approach. Risk management is concerned with sizing, which is the last layer of defense. (The prescribed size might be tiny, in which case, presumably, you are doing lots of trades.)

I’m saying this because the fact that you already have a trade on is not a reason to keep it on. If you don’t want to put the trade on fresh, you should get out. There’s an opportunity cost to your capital.

If a trade you have on is not bad but just fair, then the decision comes down to whether the variance is acceptable. If there are costs to getting out of a coin flip that you can sweat the risk on, then it’s ok to save the transaction costs. You can refine that a bit to “is the coin flip’s expectancy the same as my cost of capital” yadda yadda, but you get the gist. There’s a cost to reducing variance (ie hedging or closing) and it’s perfectly fine tto avoid it if the risk is tolerable. There are a lot of risks in life you don’t bother hedging.

Finally, rules aside, if you are regularly running risk that makes you lose sleep, impairs your judgement, or threatens to blow you up even 1% of the time, the size is wrong. 1 in a 100 is inevitable if you plan on doing this for awhile.

Positive delta puts in the wild: Avis stock (CAR)

Remember that chart of CAR last week.

(Matt Levine wrote about the fundamentals of the squeeze on 4/15)

So this was Thursday:

TradingView chart
Created with TradingView

 

Also, note that the change in the basis per expiry increased beyond October, meaning the implied carry cost is no longer negative.

When a stock is hard-to-borrow, its options will imply a future price below the spot price, since a market-maker that is getting saddled with long calls, and short puts from the flow must short shares to hedge. The cost to borrow those shares is reflected in the synthetic futures (ie the option combo of long call/short put on the same strike).

The carry rate increased on Thursday, which means puts fell relative to calls on the same strike, as presumably the borrow will loosen as the squeeze subsides. This was another headwind for people who bought downside puts to bet on CAR coming back to earth. Far OTM December puts, like the 70 strike, actually declined in value on the sell-off. A classic example of what I call positive delta puts.

“broken window theory” only applies to blue-collar crime

At least once a day, I think about how the staunchest supporters of “broken window theory” must think it only applies to blue-collar crime.

Visible law and order gets our attention, while real power funneled through shell companies and senators’ pens is hard to trace. These are old themes often set to music and poetry by Dylan, Marley, Cash, Springsteen, Queensryche (sorry, I had to slip in my personal choice — the Operation Mindcrime album).

But what’s jarring is that…well, it’s not even hard to trace.

Or what about futures markets? Those centralized exchanges have lot level surveillance of every trade. Maybe they’re afraid to open their eyes because it’s right in front of them.

Talking to friends running commodity books and the blatant abuse of futures before the Truth Social announcements is just a joke at this point. Traders are piggy-backing too but it feels like blood money. You’re sad to make it, but also your job is to make money come out of the computer.

It’s easy to rationalize that this is not blood money anyway. You’re not the source of the corruption. You’re a distant observer drafting on it, but you know you’re not in control. You could become collateral damage of the next manipulation. It’s almost like you better make money when you’re seeing the ball because you’re aware you could be on the wrong end of a random whim.

More and more, I think the left/right polarization is just bread and circuses to distract us from an Epstein class vs everyone else. Power haves and have-nots. That there happen to be deep ideologues from both red and blue varieties is pure convenience for the puppeteer. A believer without any real power is just a pawn.

Don’t let the words distract you from the actions. Via ABC reporting…

Words:

Trump was asked on Thursday if he was concerned about online prediction markets, through which bets are regularly placed on geopolitical events, such as the war in Iran, and the potential for insider trading.

“Well, you know, the whole world, unfortunately, has become somewhat of a casino,” Trump responded. “And you look at what’s going on all over the world, in Europe and every place, they’re doing these betting things. I was never much in favor of it. I don’t like it conceptually, but it is what it is.”

“But they have all these different sites. They have predictive markets. It’s a crazy world. It’s a much different world than it was.”

Actions:

One of Trump’s namesake companies, Trump Media and Technology Group, announced last year that it would launch a prediction betting marketplace called Truth Predict. The White House has said all of President Trump’s assets, including his majority stake in Trump Media and Technology Group, are being held in a trust controlled by his sons.

Polymarket has cultivated close ties to the Trump family, announcing last August that the president’s son, Donald Trump Jr., would join its advisory board. Trump Jr.’s venture capital firm, 1789 Capital, also invested in Polymarket.

Maybe owning stakes in prediction markets is just Trump hedging his lament that the world is now a casino. Great emotional awareness, I guess?

Look, if politics are your personality and you’re not manipulating them for profit, you are a sucker. If you are, you’re something else. But it’s not a sucker.

Which leaves a rhetorical question for you to ponder…what’s worse than being a sucker?

the “obvious error” rule

From @buccocapital on Anthropic CEO’s insistence that AI is going to wipe out 50% of jobs.

Bingo.

The “we gave you our data and you used used it take our livelihoods” hasn’t even become a broad movement yet. The limit of the movement would be “Sorry, but this thing you built belongs to all of us in the same sense as a national park,” and the rolling protests from industry to industry as they get wiped will be sure to inform the politicians of their preferences.

The caricature black-and-white thinker’s retort is “Well, that’s how the cookie crumbles.” But even stock exchanges, bastions of capitalism, have “obvious error rules” that use a mix of guidelines and metrics to deem certain trades as clearly erroneous, not what any reasonable trader could have intended, or just out of bounds. They have the discretion and authority to bust or adjust such trades.

A view from the comments:

If Dario is right, society is gonna invoke an “obvious error”. That’s nice that you nerds figured all this out, but your optimization function didn’t know how to count human flourishing, and as far as we can tell, there’s a bunch of you who don’t even consider this a goal. It’s also creepy that you wouldn’t hide that. A gangster surprise strangles you from behind while you’re in the front seat. A supervillain tells you their whole plan to your face before they push the button.

You’ve probably seen this floating around. Extinctionists? Good grief, look who these people are:

Image

So does Dario even want to be right about 50% of people losing their jobs? If he’s wrong, he’ll have to just live with being a regular old billionaire. I don’t know if that’s enough for him. If he is sounding the alarm on the risk and not just pumping Anthropic’s products, then he actually is being a virtuous Cassandra and maybe he just sees himself on a runaway train of prisoner’s dilemma defection.

If he thinks he can thread the needle and have everything he wants, well, I guess he’s no different than any loud mega titans these days.

Moontower #312

In this issue:

  • obvious error rule
  • broken window theory
  • why home prices aren’t going to crash
  • put options on CAR

Friends,

From @buccocapital on Anthropic CEO’s insistence that AI is going to wipe out 50% of jobs.

Bingo.

The “we gave you our data and you used used it take our livelihoods” hasn’t even become a broad movement yet. The limit of the movement would be “Sorry, but this thing you built belongs to all of us in the same sense as a national park,” and the rolling protests from industry to industry as they get wiped will be sure to inform the politicians of their preferences.

The caricature black-and-white thinker’s retort is “Well, that’s how the cookie crumbles.” But even stock exchanges, bastions of capitalism, have “obvious error rules” that use a mix of guidelines and metrics to deem certain trades as clearly erroneous, not what any reasonable trader could have intended, or just out of bounds. They have the discretion and authority to bust or adjust such trades.

A view from the comments:

If Dario is right, society is gonna invoke an “obvious error”. That’s nice that you nerds figured all this out, but your optimization function didn’t know how to count human flourishing, and as far as we can tell, there’s a bunch of you who don’t even consider this a goal. It’s also creepy that you wouldn’t hide that. A gangster surprise strangles you from behind while you’re in the front seat. A supervillain tells you their whole plan to your face before they push the button.

You’ve probably seen this floating around. Extinctionists? Good grief, look who these people are:

Image

So does Dario even want to be right about 50% of people losing their jobs? If he’s wrong, he’ll have to just live with being a regular old billionaire. I don’t know if that’s enough for him. If he is sounding the alarm on the risk and not just pumping Anthropic’s products, then he actually is being a virtuous Cassandra and maybe he just sees himself on a runaway train of prisoner’s dilemma defection.

If he thinks he can thread the needle and have everything he wants, well, I guess he’s no different than any loud mega titans these days.

broken window theory

At least once a day, I think about how the staunchest supporters of “broken window theory” must think it only applies to blue-collar crime.

Visible law and order gets our attention, while real power funneled through shell companies and senators’ pens is hard to trace. These are old themes often set to music and poetry by Dylan, Marley, Cash, Springsteen, Queensryche (sorry, I had to slip in my personal choice — the Operation Mindcrime album).

But what’s jarring is that…well, it’s not even hard to trace.

Or what about futures markets? Those centralized exchanges have lot level surveillance of every trade. Maybe they’re afraid to open their eyes because it’s right in front of them.

Talking to friends running commodity books and the blatant abuse of futures before the Truth Social announcements is just a joke at this point. Traders are piggy-backing too but it feels like blood money. You’re sad to make it, but also your job is to make money come out of the computer.

It’s easy to rationalize that this is not blood money anyway. You’re not the source of the corruption. You’re a distant observer drafting on it, but you know you’re not in control. You could become collateral damage of the next manipulation. It’s almost like you better make money when you’re seeing the ball because you’re aware you could be on the wrong end of a random whim.

More and more, I think the left/right polarization is just bread and circuses to distract us from an Epstein class vs everyone else. Power haves and have-nots. That there happen to be deep ideologues from both red and blue varieties is pure convenience for the puppeteer. A believer without any real power is just a pawn.

Don’t let the words distract you from the actions. Via ABC reporting…

Words:

Trump was asked on Thursday if he was concerned about online prediction markets, through which bets are regularly placed on geopolitical events, such as the war in Iran, and the potential for insider trading.

“Well, you know, the whole world, unfortunately, has become somewhat of a casino,” Trump responded. “And you look at what’s going on all over the world, in Europe and every place, they’re doing these betting things. I was never much in favor of it. I don’t like it conceptually, but it is what it is.”

“But they have all these different sites. They have predictive markets. It’s a crazy world. It’s a much different world than it was.”

Actions:

One of Trump’s namesake companies, Trump Media and Technology Group, announced last year that it would launch a prediction betting marketplace called Truth Predict. The White House has said all of President Trump’s assets, including his majority stake in Trump Media and Technology Group, are being held in a trust controlled by his sons.

Polymarket has cultivated close ties to the Trump family, announcing last August that the president’s son, Donald Trump Jr., would join its advisory board. Trump Jr.’s venture capital firm, 1789 Capital, also invested in Polymarket.

Maybe owning stakes in prediction markets is just Trump hedging his lament that the world is now a casino. Great emotional awareness, I guess?

Look, if politics are your personality and you’re not manipulating them for profit, you are a sucker. If you are, you’re something else. But it’s not a sucker.

Which leaves a rhetorical question for you to ponder…what’s worse than being a sucker?


Money Angle

🔗 Why Home Prices Won’t Crash: The Truth About Wall Street | 6 min read

Daryl Fairweather, Redfin’s chief economist, explains that the housing market “is really weak”, but why she doesn’t expect prices to fall. She does expect housing to be dead money for the next decade. They have been dead money in my area since the dust settled after the spike in mortgage rates in 2022.

She explains how both supply and demand pictures shape her story, as well as the large role of trapped equity. I’ve explained the math of this in depth in if you have a low rate mortgage, you incinerate money when you sell.

🔗 Money Stuff Archive

@rabbijacob16 sent me the thing I’ve been saying someone should build:

a searchable archive of Matt Levine’s Money Stuff column that automatically updates, organizes by theme, and even generates blog posts.


Money Angle for Masochists

Remember that chart of CAR last week.

(Matt Levine wrote about the fundamentals of the squeeze on 4/15)

So this was Thursday:

TradingView chart
Created with TradingView

 

Also, note that the change in the basis per expiry increased beyond October, meaning the implied carry cost is no longer negative.

When a stock is hard-to-borrow, its options will imply a future price below the spot price, since a market-maker that is getting saddled with long calls, and short puts from the flow must short shares to hedge. The cost to borrow those shares is reflected in the synthetic futures (ie the option combo of long call/short put on the same strike).

The carry rate increased on Thursday, which means puts fell relative to calls on the same strike, as presumably the borrow will loosen as the squeeze subsides. This was another headwind for people who bought downside puts to bet on CAR coming back to earth. Far OTM December puts, like the 70 strike, actually declined in value on the sell-off. A classic example of what I call positive delta puts.


Options Education in 90 Minutes

I joined a private chat with experienced traders, although not necessarily option traders. They were all very welcoming and several of them made sure to tell me that this video was formative in helping them learn about options:

I looked it up and noticed it’s approaching 10k views which isn’t much in any grand sense, but it is by far my most watched YT vid. I read the comments and even they are extremely nice so yea just throwing it out there that a bunch of nerds thought is was helpful and material that is very hard to come across online.

There’s a lot of blocking and tackling in it, but as I re-skimmed it, the part that I think is most interesting is the “dissection” stuff towards the end. I’m a bit repetitive but these are unscripted and apparently I can’t remember whatever the hell I just said so just listen at 1.5x.

This Week In The Options Trench

A practical episode for anyone who wants to understand the “shape” of realized volatility and how that informs your expectation of option p/l.

Stay groovy

☮️


Moontower Weekly Recap

creation and extraction

I’ll open with a thought that could probably just be a tweet on the limitation of markets.

I forget where I heard it, but it’s the idea that in capitalism, your wealth is a measure of “fucks given”. Did you give people what they want?

Ok. This isn’t wrong in the same way it’s not wrong to say ice cream comes from cows. It just leaves a lot out.

The 2 economic ideas that muddy the picture are consumer surplus and externalities. Consumer surplus lies on a spectrum depending on how competitive or monopolistic a particular market is. It’s not enough to create value to get paid, you have to also extract the value. If you’re in finance, how many underperforming asset gatherers do you know that would blow away the celebrity net worth of some of your favorite artists, musicians, authors, or actors. The value created vs extracted channel is very lossy.

The mediation of value created vs extracted is also downstream of rules, some of which are extremely sharp divides. Think of college athletes. They’ve always created tremendous value for their universities and alumni, but one day the most they can get is a scholarship and the next they can sign 7-figure NILs. Many of these athletes who don’t end up going pro are earning more in college than they ever will in their jobs later in life. Their value didn’t change. But their bargaining position did once their upside was allowed to float.

Finally, there are externalities. There’s a lot of rich Lee Garner Jrs out there. Or how about this one:

If you want a spicy example, just remember that a decent portion of the population would put pharma companies producing vaccines on this list.

Finally, you have businesses that derive the bulk of their income from a small percentage of their customers. The addicts power users. From Zynga-like game companies, to modern versions of casinos ranging from brokerages, exchanges, and even card companies like Panini. I’m sure TB12 is getting into a great business that’s gonna make him even richer. You can decide if every dollar made in his life created the same amount of value.