Delta-hedged risk reversals

We recently added multi-leg support to our Attribution Visualizer, our tool for allowing you to track an option contract’s p/l assuming you hedged the delta daily. The tool breaks out the p/l according to gamma + theta (which sum to realized p/l) and to implied vol (vega p/l).

With multi-leg support, you can now entertain yourself with countless questions. Like “how would a masochistic skew trade work out if I trade a risk reversal and hedge daily?”

I ran a few risk reversals through the attribution tool.

USO: Buy call/sell put after the Iran war started

Date: March 13

Expiry: June 18, 2026 (~ 3 months)

Spot: $119.92

Risk reversal: 140c / 100p (equidistant strikes ~ each 17% OTM)

Initial hedge: Short 73 shares per risk reversal (the RR had .73 delta)

The war had already flipped the skew hard toward upside strikes. The $140 call traded 94% vol against the $100 put’s 83% IV. It cost $5.83 in option premium.

At expiration, the stock expired at $114.87

So how did it work out to buy the premium IV?

moontower.ai
moontower.ai

Not good. The cumulative delta-hedged p/l was a loss of over $4.50 as you lost to both realized vol and vega. At the initiation of the trade, paying the premium vol meant you were flattish gamma but paying theta.

You were also long vega because, despite the options being equidistant, at a generally elevated vol level the lognormality of the underlying distribution and its associated positive skew pumps up the delta of calls. In fact, the 140 call was ~.47 while the 100 put, which is closer in dollar space, was only .27d. The higher call delta says the 140 strike is much “closer in vol space”. That’s why the equidistant risk reversal cost so much premium to buy the call. You are buying at OTM that has a delta that we usually associate with near ATM options!

Let’s adjust the strikes so that our call and put are both ~.25d

To equalize deltas against the $100 put you have to buy…drum roll please…

The $190 call! 58% OTM for 101% IV. Now you collect a $2.17 credit to own the call and short the 100 put. Your initial Greeks mostly vanish.

The trade still loses, but it fares much better as the loss is only $1.29.

It’s tempting to conclude paying a premium vol doesn’t work. But if you bought the much cheaper call and shorted the put on a hedged riskie in SPY before the war started, then you got smoked if you chose April 30th expiry (SPY bottomed the last day of Q1), recovered once the market started rallying, only to lose again as the market…continued rallying! SPY riskie:

moonotwer.ai

I’ve said it repeatedly over the years in different ways, but riskies are the whips and leather of the option world. If you bought the call on the SPY Feb 720/650 risk reversal on the first trading day of the year and hedged daily until expiration, you actually would have lost $.25 despite the following:

  • the trade collected about $2.75 in premium at the outset
  • the stock’s closing prices stayed inside the range of $675-$700
  • the call you bought was 10.2% IV and the put you sold was 16.8% IV
moontower.ai

In Financial Hacking, Philip Maymin invents an optimistic junior trading assistant who sits down his bosses at the bank to explain that he has found an infinite money machine. Selling the high IVs in SPY puts and buying the cheap IV in SPY calls. Maymin asks the reader to figure out why this logic doesn’t work.

Our tool provides the day-by-day audit which feeds the charts. Armed with that, Claude does an admirable job of not only answering Maymin’s prompt to the reader but also pinpointing exactly which days carry the biggest weight in the answer.

VIX and buy signals

Here’s Victor Haghani:

A high VIX1 is widely considered to be one of the cleaner buy signals out there. A recent piece in The Financial Times made the case directly: when the VIX climbs above 30, forward returns have been well above average, positive most of the time, with double-digit six-month gains.

The Financial Times case is “buy the f’n dip” logic with a VIX gate. It’s exactly the type of thing that a layreader numbly nods at when the SPX is sitting near an all-time high. The Financial Times’ case is lazy from the perspective of both investors and active traders. For the investor, it’s just survivorship bias. Knowing what we know now every pullback has just presented a bargain. The market literally “going on sale” like it’s Prime day. VIX spikes over 30 just coincide with the sales.

The question you care about is one that an active trader hearing that statement would think to hypothesis test. Given that buying any time before an all-time-high has been worked out well, how do I distinguish between relatively better or worse buys?

Back to Victor:

What that leaves out is risk. Buying the spike means taking on a lot more of it, and the strategies that did the opposite, trimming exposure when fear ran high, held up better. So the popular signal may have it backwards.

Raw returns aren’t the right thing to optimize. You care about compounded returns since investing is a repeated game. Compounded returns are risk-adjusted returns because a geometric growth process penalizes volatility.

Elm Wealth tests FT’s claim not on raw return but Sharpe Ratio, or how much return you’re getting per unit of risk taken, as the variable to maximize if we care about risk-adjusted returns.

When Fear Spikes, Should You Buy? Elm Wealth | 5 min read

What they found when they ran the numbers on S&P 500 and VIX data from 1990–2026, they found:

  • A plain static stock/T-bill portfolio: Sharpe ratio of 0.50
  • A strategy that buys more when VIX > 30% (the popular advice): 0.47 which is slightly worse than the null case
  • A strategy that reduces exposure when VIX is high (inverse sizing): 0.54
  • A simple momentum strategy (cut exposure when the market is falling, which is typically when VIX is elevated): 0.59 — the best performer

It’s always bears repeating how risk scales:

When volatility doubles, the risk of holding stocks is actually four times as large (because variance, not standard deviation, is what matters to risk).

To merely hold your position when VIX doubles, expected returns would need to quadruple. To justify doubling down, they’d need to increase eightfold, which the authors deem practically implausible.

This post led to some smart quants chiming in on X.

Here’s @ptuomov:

VIX AND EQUITY WEIGHT

The correct time to take more equity risk is when VIX has been high for six months but has been trending down. The correct time to take less equity risk is when VIX has been low for six months but has been trending up.

The target equity weight is then proportional to the target equity risk divided by VIX. Therefore, at most times, low VIX corresponds to high equity weight and high VIX to low equity weight.

This is a very low-resolution statement because each word represents many variable choices when you get into research:

Define “high”, define “trending”, “six months” was probably just a placeholder term

The degrees of freedom on the choice notwithstanding, the idea makes sense:

You are using the signals from the derivatives market, a place where leverage attracts early movers and smart money, to give a leading indicator on “the market environment is changing from the status quo” and collective anchoring biases make the wider market underreact. The way to profit from the seeds of this new information is to follow the trend.

There’s that line what the wise man does in the beginning, the fool does in the end.

The quant view is trying to find the signal of moving from the end of one cycle to the beginning of another. Trend following in a sense has a long option flavor. The premium is all the false starts and the payoff is when you finally catch a trend.

Meanwhile, buying the dip is a short option strategy in that it is betting on mean reversion as opposed to further divergence. Buying stock when VIX spikes is a mean reversion trade. But when you examine that as a strategy from the vantage point of all-time highs, it takes for granted that the mean is a good thing.

When you read a claim about a course of action, it’s good mental hygiene to first triage it as: is this directionally long or short vol?

Moontower #319

In this issue:

  • free lunches and non-tradeoffs
  • VIX and buy signals
  • delta-hedged risk reversals

Friends,

As one of my favorite HS teachers used to say, every silver lining has a cloud. (That this is one of my favorite teachers, you could probably predict my teenage affection level for rainbows and pop music). It seems I was destined to take to the idea of no free lunch easily.

Costs and Benefits

Trader and author Brent Donnelly, like most of us, struggles with the drawbacks of the otherwise transformative tech packed into our smartphones.

I Want It, But I Don’t Like It | 8 min read

The shocking and amazing thing about the unprecedented economic success of surveillance capitalism is how easily many of us (including me) surrendered to the extraction layer without much of a thought or a fight.

It’s a great example of what DFW called our default groove or “water”. That he’d spend the commencement speech warning us about lapsing into zombie mode BEFORE the smartphone was even invented indicates just how hard it really would be to overcome infinite scroll.

The short book I most commonly recommend to people is Neil Postman’s lengthy essay Amusing Ourselves To Death (my notes). It was published in 1985. My edition as a prophetic foreword:

We were keeping our eye on 1984. When the year came and the prophecy didn’t, thoughtful Americans sang softly in praise of themselves. The roots of liberal democracy had held. Wherever else the terror had happened, we, at least, had not been visited by Orwellian nightmares.

But we had forgotten that alongside Orwell’s dark vision, there was another – slightly older, slightly less well-known, equally chilling: Aldous Huxley’s Brave New World. Contrary to common belief even among the educated, Huxley and Orwell did not prophesy the same thing. Orwell warned that we would be overcome by an externally imposed oppression. But in Huxley’s vision, no Big Brother is required to deprive people of their autonomy, maturity, and history. As he saw it, people will come to love their oppression, to adore the technologies that undo their capacities to think.

What Orwell feared were those who would ban books. What Huxley feared was that there would be no reason to ban a book, for there would be no one who wanted to read one. Orwell feared those who would deprive us of information. Huxley feared those who would give us so much that we would be reduced to passivity and egoism. Orwell feared that the truth would be concealed from us. Huxley feared the truth would be drowned in a sea of irrelevance. Orwell feared we would become a captive culture. Huxley feared we would become a trivial culture, preoccupied with some equivalent of the feelies, the orgy porgy, and the centrifugal bumblepuppy. As Huxley remarked in Brave New World Revisited, the civil libertarians and rationalists who are ever on the alert to oppose tyranny “failed to take into account man’s almost infinite appetite for distractions.” In 1984, Huxley added, people are controlled by inflicting pain. In Brave New World, they are controlled by inflicting pleasure. In short, Orwell feared that what we hate will ruin us. Huxley feared that what we love will ruin us. This book is about the possibility that Huxley, not Orwell, was right.

Brent offers his Easy, Medium, Hard interventions to combat his phone. I share the struggles and have had with various levels of success tried many of these myself.

While the article is ultimately practical, I appreciated Brent’s abstract observation that the phone has both an extraction layer designed to monetize your attention as well as an agnostic technological utility layer (phone, camera, processing). His strategy is to minimize the former while maintaining the benefits of the latter. In other words, this is not the realm of a tradeoff.

In The Sydney Opera House Exam Question Dan Davies writes:

I find that the language of tradeoffs is often used in a rather bullying way. If you listen to people who are objecting to something, it’s rare that they don’t understand that there are tradeoffs in policy. They just don’t think it’s worth it. Or they think that the costs are falling disproportionately on them for benefits that go somewhere else. People think that they are sounding wise when they say that “the public want nice things but don’t want to pay for them”. But that’s just what the words “nice things” and “paying” mean. Everyone wants nice things, and nobody wants to pay, they used to teach you this when you did an economics degree.

You are almost certainly not at the efficient frontier of managing your phone’s costs and benefits.

So there must be a free lunch after all. Check out Brent’s interventions.


Accelerated upskilling

Wednesday’s oh well included some links about learning and upskilling. Here’s another one I’ve come across since:

How to ‘git gud’ at Games (Faster Than Everyone Else) 4 min read

This is from SIG’s gaming blog.

“One of the least efficient ways to improve at a game is simply playing it.”

In our latest gaming blog, Adam, a competitive gamer who has reached Master rank with all races in StarCraft II, cracked the top 50 in North America in Hearthstone Battlegrounds, and is currently ranked #1 in the world in Patchwork on BGA, looks at how you can “git gud” at games (faster than everyone else, of course).

It offers 5 tips to accelerate learning. Actually, “tips” is a flaccid description of Adam’s suggestions. They are the difference between the preparation of amateurs and pros in any skill-based activity. It’s more like an advantage loop. Combining it with talent (which is why matching your activities to your abilities is so important) and persistence is a very simple recipe to achieving rare outcomes.

I didn’t say easy. Just simple.


Maxen-Art

This past weekend I stood up a website for 10-year old to host his art. In the age of AI this is easy even without a website builder.

I bought the domain name on Namecheap, Max found gallery sites he liked that were minimalist, and I told Claude to mimic the format. The HTML is produced is hosted on Github along with a folder where we upload his images. Vercel is the host serving the webpage. There is an automatic webhook from Git to Vercel so that anytime Git updates, Vercel updates the page.

🔗maxen-art.com

 


Money Angle

Here’s Victor Haghani:

A high VIX1 is widely considered to be one of the cleaner buy signals out there. A recent piece in The Financial Times made the case directly: when the VIX climbs above 30, forward returns have been well above average, positive most of the time, with double-digit six-month gains.

The Financial Times case is “buy the f’n dip” logic with a VIX gate. It’s exactly the type of thing that a layreader numbly nods at when the SPX is sitting near an all-time high. The Financial Times’ case is lazy from the perspective of both investors and active traders. For the investor, it’s just survivorship bias. Knowing what we know now every pullback has just presented a bargain. The market literally “going on sale” like it’s Prime day. VIX spikes over 30 just coincide with the sales.

The question you care about is one that an active trader hearing that statement would think to hypothesis test. Given that buying any time before an all-time-high has been worked out well, how do I distinguish between relatively better or worse buys?

Back to Victor:

What that leaves out is risk. Buying the spike means taking on a lot more of it, and the strategies that did the opposite, trimming exposure when fear ran high, held up better. So the popular signal may have it backwards.

Raw returns aren’t the right thing to optimize. You care about compounded returns since investing is a repeated game. Compounded returns are risk-adjusted returns because a geometric growth process penalizes volatility.

Elm Wealth tests FT’s claim not on raw return but Sharpe Ratio, or how much return you’re getting per unit of risk taken, as the variable to maximize if we care about risk-adjusted returns.

When Fear Spikes, Should You Buy? Elm Wealth | 5 min read

What they found when they ran the numbers on S&P 500 and VIX data from 1990–2026, they found:

  • A plain static stock/T-bill portfolio: Sharpe ratio of 0.50
  • A strategy that buys more when VIX > 30% (the popular advice): 0.47 which is slightly worse than the null case
  • A strategy that reduces exposure when VIX is high (inverse sizing): 0.54
  • A simple momentum strategy (cut exposure when the market is falling, which is typically when VIX is elevated): 0.59 — the best performer

It’s always bears repeating how risk scales:

When volatility doubles, the risk of holding stocks is actually four times as large (because variance, not standard deviation, is what matters to risk).

To merely hold your position when VIX doubles, expected returns would need to quadruple. To justify doubling down, they’d need to increase eightfold, which the authors deem practically implausible.

This post led to some smart quants chiming in on X.

Here’s @ptuomov:

VIX AND EQUITY WEIGHT

The correct time to take more equity risk is when VIX has been high for six months but has been trending down. The correct time to take less equity risk is when VIX has been low for six months but has been trending up.

The target equity weight is then proportional to the target equity risk divided by VIX. Therefore, at most times, low VIX corresponds to high equity weight and high VIX to low equity weight.

This is a very low-resolution statement because each word represents many variable choices when you get into research:

Define “high”, define “trending”, “six months” was probably just a placeholder term

The degrees of freedom on the choice notwithstanding, the idea makes sense:

You are using the signals from the derivatives market, a place where leverage attracts early movers and smart money, to give a leading indicator on “the market environment is changing from the status quo” and collective anchoring biases make the wider market underreact. The way to profit from the seeds of this new information is to follow the trend.

There’s that line what the wise man does in the beginning, the fool does in the end.

The quant view is trying to find the signal of moving from the end of one cycle to the beginning of another. Trend following in a sense has a long option flavor. The premium is all the false starts and the payoff is when you finally catch a trend.

Meanwhile, buying the dip is a short option strategy in that it is betting on mean reversion as opposed to further divergence. Buying stock when VIX spikes is a mean reversion trade. But when you examine that as a strategy from the vantage point of all-time highs, it takes for granted that the mean is a good thing.

When you read a claim about a course of action, it’s good mental hygiene to first triage it as: is this directionally long or short vol?

Money Angle For Masochists

We recently added multi-leg support to our Attribution Visualizer, our tool for allowing you to track an option contract’s p/l assuming you hedged the delta daily. The tool breaks out the p/l according to gamma + theta (which sum to realized p/l) and to implied vol (vega p/l).

With multi-leg support, you can now entertain yourself with countless questions. Like “how would a masochistic skew trade work out if I trade a risk reversal and hedge daily?”

I ran a few risk reversals through the attribution tool.

USO: Buy call/sell put after the Iran war started

Date: March 13

Expiry: June 18, 2026 (~ 3 months)

Spot: $119.92

Risk reversal: 140c / 100p (equidistant strikes ~ each 17% OTM)

Initial hedge: Short 73 shares per risk reversal (the RR had .73 delta)

The war had already flipped the skew hard toward upside strikes. The $140 call traded 94% vol against the $100 put’s 83% IV. It cost $5.83 in option premium.

At expiration, the stock expired at $114.87

So how did it work out to buy the premium IV?

moontower.ai
moontower.ai

Not good. The cumulative delta-hedged p/l was a loss of over $4.50 as you lost to both realized vol and vega. At the initiation of the trade, paying the premium vol meant you were flattish gamma but paying theta.

You were also long vega because, despite the options being equidistant, at a generally elevated vol level the lognormality of the underlying distribution and its associated positive skew pumps up the delta of calls. In fact, the 140 call was ~.47 while the 100 put, which is closer in dollar space, was only .27d. The higher call delta says the 140 strike is much “closer in vol space”. That’s why the equidistant risk reversal cost so much premium to buy the call. You are buying at OTM that has a delta that we usually associate with near ATM options!

Let’s adjust the strikes so that our call and put are both ~.25d

To equalize deltas against the $100 put you have to buy…drum roll please…

The $190 call! 58% OTM for 101% IV. Now you collect a $2.17 credit to own the call and short the 100 put. Your initial Greeks mostly vanish.

The trade still loses, but it fares much better as the loss is only $1.29.

It’s tempting to conclude paying a premium vol doesn’t work. But if you bought the much cheaper call and shorted the put on a hedged riskie in SPY before the war started, then you got smoked if you chose April 30th expiry (SPY bottomed the last day of Q1), recovered once the market started rallying, only to lose again as the market…continued rallying! SPY riskie:

moonotwer.ai

I’ve said it repeatedly over the years in different ways, but riskies are the whips and leather of the option world. If you bought the call on the SPY Feb 720/650 risk reversal on the first trading day of the year and hedged daily until expiration, you actually would have lost $.25 despite the following:

  • the trade collected about $2.75 in premium at the outset
  • the stock’s closing prices stayed inside the range of $675-$700
  • the call you bought was 10.2% IV and the put you sold was 16.8% IV
moontower.ai

In Financial Hacking, Philip Maymin invents an optimistic junior trading assistant who sits down his bosses at the bank to explain that he has found an infinite money machine. Selling the high IVs in SPY puts and buying the cheap IV in SPY calls. Maymin asks the reader to figure out why this logic doesn’t work.

Our tool provides the day-by-day audit which feeds the charts. Armed with that, Claude does an admirable job of not only answering Maymin’s prompt to the reader but also pinpointing exactly which days carry the biggest weight in the answer.

I’m excited about the tool even though using it feels like performing surgery on myself. Which weirdly reminds me, I have an option trivia question for readers who made it this far:

POLL

What is a gut strangle?

a strangle without a delta hedge
a strangle with ITM calls and puts
a strangle spanning 2 expiries
a strangle traded before earnings
a strangle spanning 2 underlyings
19 VOTES · 20 HOURS REMAINING · SHOW RESULTS

Moontower.ai note

We will wire up the attribution function to the Moontower API which the MCP can also access so you bulk study multi-leg delta-hedged trades.

We are in the midst of a large round of discussions with traders, brokers, and advisors ahead of our next wave of expansion. Reach out if you want to discuss your workflows to see if we can help you make better or faster decisions.

Stay groovy

☮️


Moontower Weekly Recap

The Scaling Laws of Risk-Reduction

In a misconception about harvesting volatility, you learn that you do NOT need to scalp the gamma to isolate the vol of an option trade.

If you buy options implying a daily vol of 2% per day and it moves 4% per day, your expectancy is positive regardless of whether you hedge or not. That doesn’t mean you will win any more than it means you will win if you flip a fair coin and receive 2-1 odds. You have made Sklansky bucks, not necessarily real bucks.

RIP Sklansky

Hedging reduces the p/l variation around the expectancy.

In Financial Hacking, Philip Maymin explains

The inability to hedge perfectly continuously impacts your trading by introducing random risk. This risk decreases if you hedge more frequently, but only as fast as the square root. Therefore, if you want to halve your risk, you have to hedge four times as often.

He makes this tangible and practical when he says:

Noise from hedging a one-year option on a daily basis instead of continuously is about the same as one volatility point. If you make one volatility point in expected profit and the standard deviation of your profit is one volatility point, then your Sharpe ratio is about one.

His final point echoes my argument that a requirement to hedge to isolate vol is a misconception:

The risk from not hedging continuously can be diversified away.

I built a simulator so you can see this scaling law in action.

An oblique insight can be witnessed if you set up the simulation with negative expectancy, ie pay 24% vol for a stock that realizes 20%. The more you hedge the more certain you lock in negative expectancy.

Doug Costa actually showed that happen in the toy example above. The investor who bought the 110 calls based on the real-world probability but then hedged by shorting the mispriced security actually assured themselves of a loss.

If you have no edge, variance is your friend. Not financial advice.

🎮Moontower Discrete Hedging Simulator

AI Traders

Any moontower.ai subscriber can prompt our trained agent. Even if you aren’t a sub you can give it a try for free. Our team plans have included an API but we just launched an MCP allowing users to connect their own AI’s to our API endpoints.

This gives users maximum flexibility. We are tuning our agent on a regular basis, but if you prefer your own tool stack and AI you have that choice now.

We use evals for automatically RLHF’ing Moontower Agent and I also have a manual process where I give the agent and the MCP (using Claude Code) the same prompt, and then judge them myself. Very old-fashioned. I’ll share more about what we’re learning from this in the future, but in the meantime, here’s a relevant article from the market-making firm Optiver:

Where AI Trading Models Work and Where They Still Fall Short (4 min read)

Optiver’s Applied AI team did a different kind of eval. They gave several leading large language models the same assessments they give human interns and junior traders.

The results indicate where LLMs excel…

  • grasping trading theory
  • calculating fair value
  • recognizing risk

…and where they still stumble:

  • multi-step reasoning
  • updating beliefs on the fly
  • maximizing expected value under pressure

Even before AI was dominating the conversation, traders have always been obsessed with learning from data. A common example is in transaction analysis. Looking at the trades you did filtered by counterparty, venue, method (ie voice/electronic) as you suss out where you are most likely to be adversely selected. This is a hard problem even with structured data. For example, it might be straightforward to filter by how you do against live option orders (as opposed to delta neutral packages), but there are so many possible permutations. Should I consider how the quote was framed before the order came in? Do I treat a resting order differently than if I’m hit or lifted? Does time of day matter?

But now consider the scope of the unstructured data problem. The counterfactual. The order a broker showed me, I passed on and proceeded to trade without my participation. You’d need to record every phone call (actually this is already done for compliance reasons. In fact, when I interned at a bank in 1995 one of my tasks was to change the giant reel of tape!). But you’d need to link the audio of what the order was to the print when it hit the tape. Or track the fact that it never even traded. It’s like tracking the p/l of a non-trade that could have been. With transcription so cheap, this is feasible now, but it wasn’t when I was thinking about it. You could have traders note when they passed on a trade, but this would be so tedious that it was always a non-starter on a high-volume market-making desk.

My guess is that some trading shops might be doing things like this now (if not, you’re welcome for the idea). But this Optiver article made me wonder when trading rooms will be mic’d up. Jarvis listening to all the conversations, meetings, and debates to cheaply turn unstructured data to structured data.

Your voice, its quiver, your cadence, your pauses, your keystrokes, your glances, your heart rate. Insofar as humans will still be trading, it’s hard to imagine the data obsession that’s already penetrated the MLB not make its way to desk talent.

You’ll know singularity is close when the employee handbook stipulates bathroom breaks as the only acceptable cause to remove your electrodes. Buy stock in Gillette. Every man on a W2 will need to shave their chest for a clean connection.


Related

Elm Wealth let AI compete with humans in their popular Crystal Ball Challenge. You can give it a try yourself:

https://crystal-ball.elmwealth.com/

Elm’s founder Victor Haghani:

A couple of weeks ago we let you loose on our Crystal Ball Challenge: tomorrow’s headlines, $1 million to trade in stocks and bonds, and four AI models to beat. Humans showed up in force, logging thousands of plays and adding over 1,500 entries on the leaderboard.

Here is how the AI models are doing against human players so far:

– Claude: winning 65% of the time
– ChatGPT: 50%, a coin flip
– ️ Grok: 43%
– Gemini: 40%

Both the Wall Street Journal and The Economist covered the experiment this month, and both keyed on the same finding: the AIs are great at reading market-moving news, but they struggle to size their bets appropriately. Knowing what to trade turns out to be the easy part. Knowing how much is what trips them up.

If you have not played yet, three of the four AIs are losing more than half their matchups. Pick your fight. If you have played but not lately, your spot on the leaderboard might no longer safe.

 

And finally, just before I scheduled this to send out I came across Dwarkesh’s:

Subtitle: “Labs are throwing away the most valuable data”.

🗒️transcript

Moontower #318

In this issue:

  • summer reading
  • a bunch of option videos
  • AI Traders?

Friends,

As I mentioned on Wednesday, traveling mercifully forces me into quiet periods to read. In my normal routine, reading for pleasure can feel like an indulgence, but the combination of travel and my juvenile attachment to “summer vacation” is enough to put the guilt in remission. Of course, if you are of sound mind, you need no such permission, but just in case, here’s more than permission.

A Library of Distractions

If you are looking for recommendations for a book or show to get into this summer, this list by Chris Arnade might be just what the doctor ordered, and it opens with what I can only describe as a prescription:

I walk to learn, which is why I read, since each is a different way to do that. The Metis versus Techne split described by James C Scott, although there are plenty of other terms to describe experiential versus formal learning. I use his because I prefer the framing, which emphasizes that the two differ not only by methodology (talking versus reading) but by where that knowledge resides. Metis is the epistemology of the masses, and it is decentralized, local, and bottom-up versus Techne, which is that of the elite, and so is codified, formal, and top-down. Common sense versus book smarts, in Metis terms, and folk wisdom versus fact, in Techne terms.

Neither encompasses truth, so I believe you have to engage with both. If you focus solely on one, you will end up like the guys at the gym who never work out their legs. That analogy is especially appropriate for today’s elites, who seem to only do Techne days, never Metis, and so come out top-heavy, with spindly legs, too fragile to walk among the masses. I get it, going out into the world, dealing with people on their terms, can be intimidating to intellectuals, which has consequences, because while I value both, most people in the world are Metis, and consequently understanding it is essential, especially in a democracy.

That is one of my concerns about AI, which is that it will codify, then metastasize Techne, since that is what it draws from. Think of it as a grand aggregator of Techne, consuming it, then regurgitating its own watered-down, smoothed-out version as undeniable fact.

The History Beneath My Feet: Two Years in Valle de Bravo (21 min read)

Tiago Forte moved his family to a mountain town in Mexico. Find a quiet place or a cramped seat in coach, grab a coffee, and enjoy a captivating history lesson and a meditation on matters that actually matter.

The closing is more of a prompt than a spoiler, so I share it as enticement:

Who will we choose to become when work is not the central priority around which all others revolve? How will we decide to spend our time when most of it is not already spoken for by a job defined as “9 to 5”? How will we define ourselves when our work ceases to be an identity, and becomes more like an implementation detail?

I don’t know, but Valle de Bravo is beginning to suggest answers out of the deep well of its 500 years of history and culture.


As for me, my leisure summer reading:

Dominion fans, that book is not to be confused with:

 

And for podcasts, I’ve queued about 25 pods from Rest Is History. I just finished:

This is probably the only episode you should not listen to with the kids in the car.


Money Angle

This week’s Option Trench will be very educational to anyone whose traded an equity option since they are American-style (meaning you can exercise them early). Erik was assigned on IBIT puts 22 days before expiration and thought it was a bit strange. I agree. I think it was a sub-optimal early exercise, but in this chat you can see what factors influence the assessment of “optimal” and the surface of reasonable disagreement.

This is a link to the calculator in the video:

https://moontower.ai/tools-and-games/american-options-early-exercise

Also, Erik and I pre-recorded our Options Trench podcast episodes before I went on vacation. If you want to catch up…

📺Volatility in 5 Levels of Difficulty: An introduction to various meanings of volatility.

📺All Implied Volatility is WRONGThis one goes well right after the “vol in 5 levels of difficulty”. It’s a topic that is mathematically simple, but conceptually, I notice it just seems to warp people’s brain. I explain who does and who doesn’t need to care about it. If you are in this section, you very well might need to care.

📺An Inside Look At How SIG Trains TradersSee if you can answer some old interview questions and learn about bootcamp.

Money Angle For Masochists

Any moontower.ai subscriber can prompt our trained agent. Even if you aren’t a sub you can give it a try for free. Our team plans have included an API but we just launched an MCP allowing users to connect their own AI’s to our API endpoints.

This gives users maximum flexibility. We are tuning our agent on a regular basis, but if you prefer your own tool stack and AI you have that choice now.

We use evals for automatically RLHF’ing Moontower Agent and I also have a manual process where I give the agent and the MCP (using Claude Code) the same prompt, and then judge them myself. Very old-fashioned. I’ll share more about what we’re learning from this in the future, but in the meantime, here’s a relevant article from the market-making firm Optiver:

Where AI Trading Models Work and Where They Still Fall Short (4 min read)

Optiver’s Applied AI team did a different kind of eval. They gave several leading large language models the same assessments they give human interns and junior traders.

The results indicate where LLMs excel…

  • grasping trading theory
  • calculating fair value
  • recognizing risk

…and where they still stumble:

  • multi-step reasoning
  • updating beliefs on the fly
  • maximizing expected value under pressure

Even before AI was dominating the conversation, traders have always been obsessed with learning from data. A common example is in transaction analysis. Looking at the trades you did filtered by counterparty, venue, method (ie voice/electronic) as you suss out where you are most likely to be adversely selected. This is a hard problem even with structured data. For example, it might be straightforward to filter by how you do against live option orders (as opposed to delta neutral packages), but there are so many possible permutations. Should I consider how the quote was framed before the order came in? Do I treat a resting order differently than if I’m hit or lifted? Does time of day matter?

But now consider the scope of the unstructured data problem. The counterfactual. The order a broker showed me, I passed on and proceeded to trade without my participation. You’d need to record every phone call (actually this is already done for compliance reasons. In fact, when I interned at a bank in 1995 one of my tasks was to change the giant reel of tape!). But you’d need to link the audio of what the order was to the print when it hit the tape. Or track the fact that it never even traded. It’s like tracking the p/l of a non-trade that could have been. With transcription so cheap, this is feasible now, but it wasn’t when I was thinking about it. You could have traders note when they passed on a trade, but this would be so tedious that it was always a non-starter on a high-volume market-making desk.

My guess is that some trading shops might be doing things like this now (if not, you’re welcome for the idea). But this Optiver article made me wonder when trading rooms will be mic’d up. Jarvis listening to all the conversations, meetings, and debates to cheaply turn unstructured data to structured data.

Your voice, its quiver, your cadence, your pauses, your keystrokes, your glances, your heart rate. Insofar as humans will still be trading, it’s hard to imagine the data obsession that’s already penetrated the MLB not make its way to desk talent.

You’ll know singularity is close when the employee handbook stipulates bathroom breaks as the only acceptable cause to remove your electrodes. Buy stock in Gillette. Every man on a W2 will need to shave their chest for a clean connection.


Related

Elm Wealth let AI compete with humans in their popular Crystal Ball Challenge. You can give it a try yourself:

https://crystal-ball.elmwealth.com/

Elm’s founder Victor Haghani:

A couple of weeks ago we let you loose on our Crystal Ball Challenge: tomorrow’s headlines, $1 million to trade in stocks and bonds, and four AI models to beat. Humans showed up in force, logging thousands of plays and adding over 1,500 entries on the leaderboard.

Here is how the AI models are doing against human players so far:

– Claude: winning 65% of the time
– ChatGPT: 50%, a coin flip
– ️ Grok: 43%
– Gemini: 40%

Both the Wall Street Journal and The Economist covered the experiment this month, and both keyed on the same finding: the AIs are great at reading market-moving news, but they struggle to size their bets appropriately. Knowing what to trade turns out to be the easy part. Knowing how much is what trips them up.

If you have not played yet, three of the four AIs are losing more than half their matchups. Pick your fight. If you have played but not lately, your spot on the leaderboard might no longer safe.

 

And finally, just before I scheduled this to send out I came across Dwarkesh’s:

Subtitle: “Labs are throwing away the most valuable data”.

🗒️transcript

 

 

Stay groovy

☮️


Moontower Weekly Recap

DFW

Happy summer everyone!

It’s good to be back.

I spent the past 2 weeks traveling with my family and in-laws. 9 adults and 8 kids from ages 10 to 16. We spent the first week in Florence and Rome and the second week on a cruise that stopped in Santorini, Mykonos, Ephesus (an ancient Roman city in Turkey), and Naples. 20k steps a day was still no match for the 5 lbs I was destined to gain.

I like being in new places. I don’t especially love getting to them. But if we could teleport I wouldn’t be forced to sit and read. I’ll be sharing links and thoughts to the stuff that stood out. As books go, I read Dan Abram’s Sharp Money and re-read Brave New World (twitter thread).

The best single thing I read was also a re-read I chose since I was on a Royal Caribbean ship — David Foster Wallace’s long-form article originally published in the January 1996 Harper’s titled Shipping Out (pdf)

DFW’s x-ray mind is on full display here. His penetrating power of observation would leave you frustrated in your own blindness if he didn’t distract you by relaying the barrage of comedy that reality generously furnishes but to which we are dulled if it’s not accompanied by a laugh-track. His writing resensitizes your humor follicles.

Noticing, of course, cuts in all directions. And one particular passage shows where we are today by relief. What we accept as normal wasn’t always, but since this article is from 1996, the acceleration of a certain enshitification is more apparent. Wallace is describing the copy in the cruise brochure that the celebrated author Frank Conroy was paid to write:

Conroy’s essay is graceful and lapidary and persuasive. I submit that it is also completely insidious and bad. Its badness does not consist so much in its constant and mesmeric references to fantasy and alternate realities and the palliative powers of professional pampering—

I’d come on board after two months of intense and moderately stressful work, but now it seemed a distant memory. I realized it had been a week since I’d washed a dish, cooked a meal, gone to the market, done an errand or, in fact, anything at all requiring a minimum of thought and effort. My toughest decisions had been whether to catch the afternoon showing of Mrs. Doubtfire or play bingo.

—nor in the surfeit of happy adjectives and the tone of breathless approval throughout—

Bright sun, warm still air, the brilliant blue-green of the Caribbean under the vast lapis lazuli dome of the sky… For all of us, our fantasies and expectations were to be exceeded, to say the least. When it comes to service, Celebrity Cruises seems ready and able to deal with anything.

Rather, part of the essay’s real badness can be found in the way it reveals once again the Megaline’s sale-to-sail agenda of micro-managing not only one’s perceptions of a 7NC but even one’s own interpretation and articulation of those perceptions. In other words, Celebrity’s P.R. people go and get a respected writer to pre-articulate and endorse the 7NC experience, and to do it with a professional eloquence and authority that few lay perceivers and articulators could hope to equal. But the really major badness is that the project and placement of “My Celebrity Cruise” are sneaky and duplicitous and well beyond whatever eroded pales still exist in terms of literary ethics. Conroy’s “essay” appears as an inset, on skinnier pages and with different margins than the rest of the brochure, creating the impression that it has been excerpted from some large and objective thing Conroy wrote. But it hasn’t been. The truth is that Celebrity Cruises paid Frank Conroy up-front to write it, even though nowhere in or around the essay is there anything acknowledging that it’s a paid endorsement, not even one of the little “So-and-so has been compensated for his services” that flashes at your TV screen’s lower right during celebrity-hosted infomercials. Instead, inset on this weird essaymercial’s first page is a photo of Conroy brooding in a black turtleneck, and below the photo an author bio with a list of Conroy’s books that includes the 1967 classic Stop-Time, which is arguably the best literary memoir of the twentieth century and is one of the books that first made poor old humble yours truly want to try to learn how to be a writer.

In the case of Frank Conroy’s “essay,” Celebrity Cruises is trying to position an ad in such a way that we come to it with the lowered guard and leading chin we reserve for coming to an essay, for something that is art (or that is at least trying to be art). An ad that pretends to be art is—at absolute best—like somebody who smiles at you only because he wants something from you. This is dishonest, but what’s insidious is the cumulative effect that such dishonesty has on us: since it offers a perfect simulacrum of goodwill without goodwill’s real substance, it messes with our heads and eventually starts upping our defenses even in cases of genuine smiles and real art and true goodwill. It makes us feel confused and lonely and impotent and angry and scared. It causes despair.15

But for this particular 7NC consumer, Conroy’s ad-as-essay ends up having a truthfulness about it that I’m sure is unintentional. As my week on the Nadir wears on, I begin to see this essaymercial as a perfectly ironic reflection of the mass-market cruise experience itself. The essay is polished, powerful, impressive, clearly the best that money can buy. It presents itself as being for my benefit. It manages my experiences and my interpretation of those experiences and takes care of them for me in advance. It seems to care about me. But it doesn’t, not really, because first and foremost it wants something from me. So does the cruise itself. The pretty setting and glittering ship and sedulous staff and solicitous fun-managers all want something from me, and it’s not just the price of my ticket—they’ve already got that. Just what it is that they want is hard to pin down, but by early in the week I can feel it building: it circles the ship like a fin.

Here’s that footnote 15:

This is related to the phenomenon of the Professional Smile, a pandemic in the service industry, and no place in my experience have I been on the receiving end of as many Professional Smiles as I was on the Nadir—maître d’s, chief stewards, hotel managers’ minions, cruise director… their P.S.’s all come on like switches at my approach. But also back on land: at banks, restaurants, airline ticket counters, and on and on. You know this smile—the one that doesn’t quite reach the smiler’s eyes and signifies nothing more than a calculated attempt to advance the smiler’s own interests by pretending to like the smilee. Why do employers and supervisors force professional service people to broadcast the Professional Smile? Am I the only person who’s sure that the growing number of cases in which normal-looking people open up with automatic weapons in shopping malls and insurance offices and medical complexes is somehow causally related to the fact that these venues are well-known dissemination-loci of the Professional Smile?

Note to the next person who goes to heaven: please don’t tell Wallace that The Professional Smile is most innocent persuasion tactic in AD 2026. Let him RIP.


I urged Yinh to read the essay. She didn’t know about DFW, but after the essay she was texting some friends about it. One of her girlfriends admitted she regularly revisits this interview:

One of the comments said it best. It’s a palette cleanser.

It’s also very fun if you enjoy watching others geek out about art they love (in this case it’s DFW discussing David Lynch). It’s this marvelous thing where people cannot hold back their love for another’s work but can also articulate why. It takes me back to early teen years. Hearing an older cousin present their case for how every track on Dirt is about a different way to die. Down in a Hole is about death by…sex? It’s not important now. But then, you’re young and impressionable. You remember how fun it is to be impressionable. When the risk-reward was different. When being misled was a hazard of optimism instead of a salesman’s bullseye.

Anyway, I hadn’t really watched DFW before, so I was unaware of his mannerisms. You can tell that Jason Segal would have studied this interview to portray DFW in End of the Tour.


Years ago, I was walking out of a Trader Joe’s parking lot. The moment led to this tweet:

I never really thought about why I thought of that moment the way I did. After I recently listened to DFW’s speech below I think I know why. It’s a choice that protects my attention. I didn’t realize that until DFW pointed it. You’ll understand from the excerpt below.

Emphasis mine:

…Or I can choose to force myself to consider the likelihood that everyone else in the supermarket’s checkout line is just as bored and frustrated as I am, and that some of these people probably have harder, more tedious and painful lives than I do.

Again, please don’t think that I’m giving you moral advice, or that I’m saying you are supposed to think this way, or that anyone expects you to just automatically do it. Because it’s hard. It takes will and effort, and if you are like me, some days you won’t be able to do it, or you just flat out won’t want to.

But most days, if you’re aware enough to give yourself a choice, you can choose to look differently at this fat, dead-eyed, over-made-up lady who just screamed at her kid in the checkout line. Maybe she’s not usually like this. Maybe she’s been up three straight nights holding the hand of a husband who is dying of bone cancer. Or maybe this very lady is the low-wage clerk at the motor vehicle department, who just yesterday helped your spouse resolve a horrific, infuriating, red-tape problem through some small act of bureaucratic kindness. Of course, none of this is likely, but it’s also not impossible. It just depends what you want to consider. If you’re automatically sure that you know what reality is, and you are operating on your default setting, then you, like me, probably won’t consider possibilities that aren’t annoying and miserable. But if you really learn how to pay attention, then you will know there are other options. It will actually be within your power to experience a crowded, hot, slow, consumer-hell type situation as not only meaningful, but sacred, on fire with the same force that made the stars: love, fellowship, the mystical oneness of all things deep down.

Not that that mystical stuff is necessarily true. The only thing that’s capital-T True is that you get to decide how you’re gonna try to see it.

This, I submit, is the freedom of a real education, of learning how to be well-adjusted. You get to consciously decide what has meaning and what doesn’t. You get to decide what to worship.

Because here’s something else that’s weird but true: in the day-to-day trenches of adult life, there is actually no such thing as atheism. There is no such thing as not worshipping. Everybody worships. The only choice we get is what to worship. And the compelling reason for maybe choosing some sort of god or spiritual-type thing to worship–be it JC or Allah, be it YHWH or the Wiccan Mother Goddess, or the Four Noble Truths, or some inviolable set of ethical principles–is that pretty much anything else you worship will eat you alive. If you worship money and things, if they are where you tap real meaning in life, then you will never have enough, never feel you have enough. It’s the truth. Worship your body and beauty and sexual allure and you will always feel ugly. And when time and age start showing, you will die a million deaths before they finally grieve you. On one level, we all know this stuff already. It’s been codified as myths, proverbs, clichés, epigrams, parables; the skeleton of every great story. The whole trick is keeping the truth up front in daily consciousness.

Worship power, you will end up feeling weak and afraid, and you will need ever more power over others to numb you to your own fear. Worship your intellect, being seen as smart, you will end up feeling stupid, a fraud, always on the verge of being found out. But the insidious thing about these forms of worship is not that they’re evil or sinful, it’s that they’re unconscious. They are default settings.

They’re the kind of worship you just gradually slip into, day after day, getting more and more selective about what you see and how you measure value without ever being fully aware that that’s what you’re doing.

And the so-called real world will not discourage you from operating on your default settings, because the so-called real world of men and money and power hums merrily along in a pool of fear and anger and frustration and craving and worship of self. Our own present culture has harnessed these forces in ways that have yielded extraordinary wealth and comfort and personal freedom. The freedom all to be lords of our tiny skull-sized kingdoms, alone at the centre of all creation. This kind of freedom has much to recommend it. But of course there are all different kinds of freedom, and the kind that is most precious you will not hear much talk about much in the great outside world of wanting and achieving…. The really important kind of freedom involves attention and awareness and discipline, and being able truly to care about other people and to sacrifice for them over and over in myriad petty, unsexy ways every day.

That is real freedom. That is being educated, and understanding how to think. The alternative is unconsciousness, the default setting, the rat race, the constant gnawing sense of having had, and lost, some infinite thing.

I know that this stuff probably doesn’t sound fun and breezy or grandly inspirational the way a commencement speech is supposed to sound. What it is, as far as I can see, is the capital-T Truth, with a whole lot of rhetorical niceties stripped away. You are, of course, free to think of it whatever you wish. But please don’t just dismiss it as just some finger-wagging Dr Laura sermon. None of this stuff is really about morality or religion or dogma or big fancy questions of life after death.

The capital-T Truth is about life BEFORE death.

It is about the real value of a real education, which has almost nothing to do with knowledge, and everything to do with simple awareness; awareness of what is so real and essential, so hidden in plain sight all around us, all the time, that we have to keep reminding ourselves over and over:

“This is water.”

“This is water.”

It is unimaginably hard to do this, to stay conscious and alive in the adult world day in and day out. Which means yet another grand cliché turns out to be true: your education really IS the job of a lifetime. And it commences: now.

I wish you way more than luck.

📺The full “This is water” commencement address

In other news…

I relented. I scooped a copy of Infinite Jest while being a dutiful Prime Day consumer. I predict I won’t finish it until summer vacation 2029.

hurst

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

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

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

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

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

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

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

Net: -15k

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

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

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

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

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

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

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

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

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

We need to examine randomness.

Returning to the context of volatility scaling and its relationship to randomness, Euan reaches for a popular quant tool. The Hurst exponent. That’s why I picked H for the exponent in the general version of the volatility power law.

Euan’s definitions:

  • H = 0.5 is a random walk. No memory.
  • H < 0.5 is mean-reverting. Up tends to be followed by down.
  • H > 0.5 is trending, or “persistent.” Up tends to be followed by more up.

It’s time to do some learning moontower-style and start with the basics.

What The Hurst Exponent Actually Measures

Our Favorite Starting Point: Coin Flips

Flip a fair coin 100 times. Score +1 for heads, −1 for tails, and keep a running sum.

After 100 flips, how far from zero is that running sum?

Three stylized regimes to compare:

  • Perfectly correlated flips (every flip copies the last one): the running sum after 100 flips is ±100. It grows linearly with N.
  • Perfectly anti-correlated flips (+1, −1, +1, −1, …): the running sum never escapes ±1. It doesn’t grow with N at all.
  • Independent flips: the running sum lands around ±√N or in this case ±10.

Think of these as regimes that correspond to three scaling exponents:

  • Correlated (trending) N^1
  • Anti-correlated (mean-reverting): N^0
  • Independent (random walk) N^0.5

The exponent is the answer to “what power of N does the cumulative range scale with?”

Strip out the step size to isolate the regime

The ±1 coin gave a running sum with range around √N. If the coin paid ±10 instead, the range would be 10·√N. Bigger steps, bigger range. We want to strip out that distortion. If we measured price range on raw market data, a jumpy stock would always look more “trending” than a calm one, just because its steps are bigger. We’d be measuring volatility tangled up with regime, when we want regime alone.

The fix is to divide the range by the standard deviation of the steps: R/S

For the ±1 coin, R ≈ √N and S = 1, so R/S ≈ √N.

For the ±10 coin, R ≈ 10·√N and S = 10, so R/S ≈ √N. Same answer. The step size cancels out.

That’s the rescaled range. R/S only cares about the regime of the series, not its scale.

From coins to assets

Now we can adapt this to asset returns.

So we have two measurements over a window of T days of log returns:

  • S = the standard deviation of the returns (the step size in the coin example)
  • R = the range (max − min) of the cumulative sum of the de-meaned returns. How far the running total wandered between its high and its low.

We de-mean before computing R, so we strip out drift. We don’t care that the thing went up over the window, we care how it wandered around that trend. We divide by S to strip out the volatility scale.

The √T Benchmark

If returns are independent, R/S also grows like √T for the same underlying reason:

The variances of independent things add, so the spread grows by √T.

Now generalize it. Instead of forcing the exponent to be 0.5, let the data tell you:

R/S ~ T^H

  • H = 0.5: matches √T. Independent.
  • H > 0.5: R/S grows faster than √T. Trending. Moves reinforce each other.
  • H < 0.5: R/S grows slower than √T. Mean-reverting. Moves fight each other.

Reading H Off A Plot

The scaled range takes the functional form of a power law. If we take logs of both sides, the power law becomes a straight line, and the exponent H becomes the slope of the line.

log₂(R/S) = H · log₂(T)

Compute R/S at a few different T’s, plot them log-log, and the slope is H. It doesn’t matter which type of log we use. We could choose log₁₀ or ln, but using log₂ gives a clean way to narrate it: every time you double T, R/S multiplies by 2^H.

  • H = 0.5: each doubling multiplies R/S by √2 ≈ 1.41
  • H = 1.0: each doubling doubles R/S
  • H = 0.0: each doubling leaves R/S untouched

The Implementation Recipe

  1. Pick several T’s (say 5, 10, 20, 40).
  2. At each T, chop the sample into non-overlapping chunks. (see appendix)
  3. For each chunk: de-mean, cumulative sum, R = max − min, S = std dev, then R/S.
  4. Average R/S across the chunks at that T.
  5. Fit a line through the (log₂T, log₂(R/S)) points. The slope is H.

Worked Examples

Computing one R/S by hand

Take a single 5-day chunk of returns, in %: +1, +3, −2, +4, −1.

  1. Mean: (1 + 3 − 2 + 4 − 1) / 5 = +1%
  2. De-mean (subtract the mean from each): 0, +2, −3, +3, −2
  3. Cumulative sum (running total of the de-meaned series): 0, +2, −1, +2, 0
  4. R is the range of that running total: max − min = (+2) − (−1) = 3
  5. S is the standard deviation of the original five returns ≈ 2.28 (population stdev, STDEV.P)
  6. R/S = 3 / 2.28 ≈ 1.32

That 1.32 is one chunk’s R/S.

Notice that since √5 ≈ 2.24, this little stretch wandered less than a random walk would, so it reads mean-reverting

We just repeat this for several windows.

Say you’ve got 80 days of returns.

Compute R/S at T = 5, 10, 20, 40:

The Hurst exponent, H ≈ 0.43, is extracted as the slope from the log-log plot, which is is linear transformation of a power function.

H<.50 corresponds to mean-reversion. Every doubling of T multiplies R/S by 2^0.43 ≈ 1.35, a hair under the 1.41 you’d get from a pure random walk. The wandering is growing slower than random diffusion would predict.

Applications of H

If H isn’t 0.5, then √T annualization is wrong for that asset. H > 0.5 means your long-horizon vol is higher than √252 × daily vol claims. H < 0.5 means it’s lower.

The articles I linked to in the intro wrestle with this same idea but in a simpler point-to-point manner in the form of a trend ratio (ie vol sampled weekly ÷ vol sampled daily).

If you assume the asset is “self-similar,” then the exponent H governs the scaling at every horizon then besides looking for trend or mean reversion strategies you can now research a world of option relationships that are potentially mispriced if the assumption of independence is strongly embedded in volatility scaling models.

To be reductionist, my trend ratio calcs were a two-point estimate of H. Autocorrelation patches function as a lagged estimate of the same thing. Hurst is the version that uses the whole curve instead of two points or one lag.

The assumption that markets are self-similar is wrong. The more wrong it is, the less you have to gain from Hurst vs point-to-point extrapolations, but all of this is dominated by the biggest elephant in the room. Can past data help you predict trend or mean-reversion at all? Which just circles back to Euan. If you are going to bother trading, you must believe, at worst, they are merely “almost random”.

A Sense Of Proportion

H looks like a number between 0 and 1, so a move from 0.50 to 0.55 feels insignificant. The vol-annualization lens is the cleanest way to debunk that.

Consider a stock with 1% daily vol.

  • At H = 0.50: 1% × 252^0.5 = 15.9% annual
  • At H = 0.55: 1% × 252^0.55 = 19.4% annual

A 0.05 bump in H means a 22% increase in annualized vol. This obviously affects your opinion of option prices but it’s also meaningful for position sizing and risk or VaR.

Most equity-index Hurst estimates sit in a narrow-looking 0.45 to 0.55 band, but that “small” band obscures significant differences.

The Catch: The Naive Number Lies

Now go back to Sinclair’s warning, because this is where it earns its keep.

Classic R/S — the recipe above, the one in his book, the one everybody reaches for first — is biased. Run it on a series you know is a memoryless random walk, at a 252-day window, and it does not hand you back 0.5. It hands you back something noticeably higher. The estimator manufactures a little fake memory all on its own, before the data even gets a vote.

So when SPY’s rolling H sits below 0.5, you have to ask how much of that is the market and how much is the ruler. This isn’t a fringe complaint. Lo built a modified R/S statistic back in 1991 precisely because the classic version confuses genuine long memory with garden-variety short-range stuff like volatility clustering, and equity returns are drowning in volatility clustering.

The fix is not exotic. Simulate a big pile of random walks the same length as your estimation window, run the exact same R/S recipe on them, and see what H the estimator coughs up on data you built to have none. Whatever offset it shows is the lie. Subtract it. Now a true random walk reads 0.5, and a reading that survives the correction is one you can actually look at.

This is the same humility you already preach about your own VRP work. A single rolling-window H is one draw. Treating it as gospel is exactly the “sample size of 1” trap. Calibrate it or don’t believe it.

Sandbox

I’ve heard of many traders, including option traders using Hurst in their research. It feels like it’s accelerated in the past 5 years. I didn’t take a harder look at it until Euan gave a brief intro to it in Retail Options Trading and LLM’s made it easier to tutor yourself on a quant method. It’s a technique that’s well-known, but anecdotally I’ve heard a wide range of mileage from it (I’m guessing every pro option trader in a seat today has at least heard of it in trading contexts).

If autocorrelation adnrealized vol ratios at different frequencies are worth looking at then Hurst is worth at least “spaghetti on the wall”. I built a Jupyter notebook to tinker using yfinance data. You can use it, fork it, whatever:

https://colab.research.google.com/github/Kris-SF/data-pipelines/blob/main/quant-analysis/hurst_analysis.ipynb

If I were to bring this “in the lab” to see how it can become a metric or even signal I’d start with tinkering to see how it its output jives with my intuition of how a certain asset behaved over a particular period.

Once I had a feel for it, I’d throw the metric up on a scatterplot against other metrics to develop a sense of what is normal. Are there any correlations between H and IV skews or IV term structures? How do changes in Hurst coincide with changes in realized vol (rv is an input to R/S therefore and ultimately H so maybe we are hunting for a residual variable to track?)

If you have organized data, in the world of LLMs all of this work is more fun and faster. For now, I hope this primer on Hurst was a digestible first step for explaining the theory behind it and why it can be relevant.

You can find additional notes below.


Appendix: What “chop into non-overlapping chunks” really means

T is a window length, just how many days of wandering you measure at once. You pick several because H isn’t a property of any single window. It’s the rate at which R/S grows as the window lengthens. A handful of T’s gives you points to fit a slope through.

You have 251 daily returns. You want one number, H. That’s the entire goal.

Pick a few window sizes: 5, 10, 20, 40.

For each window size you do the exact same thing:

  • T = 5: chop the 251 days into back-to-back groups of 5. You get 50 groups. Compute R/S for each group, then average all 50. That’s your R/S at 5.
  • T = 10: chop into groups of 10. You get 25 groups. R/S for each, average them. R/S at 10.
  • T = 20: groups of 20, so 12 groups. Average. R/S at 20.
  • T = 40: groups of 40, so 6 groups. Average. R/S at 40.

Now you have four points: (5, R/S@5), (10, R/S@10), (20, R/S@20), (40, R/S@40). Plot them log-log, draw the best-fit line, and the slope is H.

You want enough windows to fit a line, but longer windows are comprised of fewer blocks (like the T=40 window) so they’re shakier sample from which you are computing an average R/S.

Appendix: Bias

The body said classic R/S reads high on a random walk.

The finite-sample problem

Even on a true coin-flip walk, R/S over a short window doesn’t average to exactly √T. It sits a little above. Hurst, Anis, and Lloyd worked out the expected R/S of a random walk in closed form back in the 70s, so one fix is to divide your measured R/S by that expected value at each T before you fit. It’s conceptually similar to the familiar Bessel n−1 adjustment done to sample variance since we don’t know the true population variance.

Claude suggested 2 ways to apply a correction:

  • Use the closed-form expected R/S directly
  • Simulate a pile of random walks and measure what your exact regression spits out.

They differ because the log of an average isn’t the average of a log (Jensen’s inequality). The closed-form route leaves a residual bias of a few hundredths. The simulation route, because it runs the identical regression you use in practice, lands a true random walk back at 0.5.

After much back-and-forth, I took Claude’s rec and had the notebook use the simulation route.

The nice thing about LLMs is they know a lot of the academic history of a measure. Like I said this is a starting point for your own exploration.

Better estimators exist.

Classic R/S is the cleanest to teach and the weakest to trade. Lo’s modified R/S (1991) is built to ignore short-range dependence like volatility clustering, which plain R/S happily mislabels as memory. Detrended Fluctuation Analysis (Peng et al., 1994) is the workhorse in the econophysics literature. If you ever size a position off an H, cross-check it with one of those rather than lean on R/S alone.

what new grads should focus on

In light of graduation season, this week’s material has been focused on a mix of inspiration and general course of action to what I would characterize as an overarching sense of thriving.

When I’m not yapping about trading or options, much of my writing or curation revolves around learning, motivation, and creativity. These 3 factors are in a continuous conversation with each other. That internal conversation has far-reaching effects because it guides our actions which in turn feed back to this internal conversation. We’re these complicated black boxes hosting billions of hormonal and electrical collisions that mean on some level we’re all the same in that we can be described generally as such a machine, but profoundly different since the infinite combinations of those reactions make us unique as, well, precious snowflakes.

Any perspective that fails to appreciate both how general and specific we are is an incomplete description of our condition. Which brings us to the fundamental tension of advice. It’s tempting to give it because on one level we’re not that different, but on another level it’s impossible for any general advice to be right-sized for any individual.

It is with this uneasy marriage of humility and hubris that I dare to offer a few thoughts for those pulling up to the staging areas of their careers. It is the same answer I give to those insistent enough to figuratively sign a waiver acknowledging all the disclaimers that an honest person would give before proffering advice.

The magical words that indicate such an insistence, an insistence which places earnestness above omniscience, which may be the best we can do in wicked domains, are “what would you tell your kids to do?”

In the face of such an approach, I’m cornered. But since I know that you know my kids are not your kids, I can trust you will be able to adapt the advice to your own or your loved ones’ situation.

What should a new grad pursue?

The number one thing a new grad should optimize for is rapid learning.

Womp, womp.

Kris, you put that behind a paywall?

Hang on.

It’s quite clear to me that this is either not as obvious as it appears OR people don’t even know what rapid learning means.

Let’s start with what it means to learn.

Actually, let’s start with what it is not.

Learning is not trivia. It’s not most of what you ever did in school. To be as charitable as possible to the institution of school, it is a survey of the pu pu platter of subjects that have achieved a depth of scholarly history for which the degree of specialization required to contribute to our collective understanding offers an ample capacity to absorb a motivated student’s talent. There is no end to biology. If it has grabbed your imagination, there is a lifelong pursuit awaiting you.

However, most people will not become academics, scholars, or scientists. Most will not chase anything formal school is instrumental for, or for which access to leading professors is important. The learning you get from school beyond the years of arithmetic and reading acquisition is mostly trivia.

[This is not a knock on trivia or, by implication, the subject of history. Thinking needs raw material to operate on. There are extreme points of view that don’t see the benefit of learning anything, since you can look stuff up. If I had to steelman that position, I’d argue that basic knowledge should be reclassified as something to acquire on demand since there’s an opportunity cost of onboarding knowledge you’ll never actually need.

But I think the extreme view is a bridge too far because there’s an irreducible arbitrariness in what will turn out to be useful knowledge. The project known as humanity seems to be an instance of a cosmic explore/exploit problem. I think there’s plenty of room to update curricula to better balance pragmatism and imagination, but as we get to the steep part of any learning ROI curve, the risk of premature optimization would overwhelm the gain in local efficiency. But insofar as I think curricula can use an OS upgrade, we’re pretty far from that point.]

So for most people, school mostly teaches trivia that they will mostly forget. The forgetting part is neither the student or the school’s fault. It’s actually a symptom of the uselessness. Knowledge is use it or lose it. If you’re losing it, it’s because you’re not using it. What odds are you willing to lay on your ability to do long division with 3-digit numbers? Can you multiply the year the Magna Carta by the atomic weight of oxygen? That “Are you smarter than a 5th grader?” was a fun show that proves the point. You might not know what a 5th grader knows, but you can still multiply 2 numbers. Use it or lose it.

Great, we’ve established that most of what we were told is learning, is actually not learning, at least according to any definition of learning worth having. Ok, here’s a definition worth having:

The assimilation of information that leads to adaptive changes in behavior

It’s only a few words, but it orients “learning” towards identifiable goals.

To go all 5th grader on you, subject:

“Assimilation of information” is not just about onboarding but also about accessible retention. You need to be able to draw the arrow from your quiver when appropriate.

Predicate:

“Leads to adaptive changes in behavior” implies that the knowledge is applied towards growth which is something that happens in the physical world, even if it starts internally. Growth is a goal. It can be as fuzzy as imagination or brain fodder, but these remain intermediate steps to change.

That change should be in the direction of desire.

This deserves a couple of comments:

  1. Getting better at crime is a desire and anti-desire depending on who you ask, so the notion of growth is neutral from a non-moral master view.
  2. The recursive nature of learning is also on display. Our desires are inputs that dictate where we spend time to learn, but also outputs that can change based on learning.

Learning is ultimately about outcomes. The concept, being morally neutral, is compatible with any metaphysical view. But being as we are literal material composed of nature’s Legos, our bodies and minds have maintenance requirements throughout our lives. Those requirements should include a surplus capacity for growth in the early years of our lives and a surplus to slow the decay in our back nine.

Rapid learning is the abstract foundation of this surplus. You can modify the terms based on context. Make it more concrete if you prefer. Savings. Redundancy. Time. All of which return to the abstract. To a benevolence at a human scale. A nest for babies, children, and the next generation to grow. To learn.

[It’s possible that this value-neutral concept of learning would not lead to benevolence but annihilation. Perhaps the pace of advance into god-like technology intercepts nature’s learning algorithm, evolution, at a time scale in which it cannot recover its goal of replication. We don’t even know if passive investing is a Taleb turkey problem, good luck with “was the die cast on our own demise when a proto-human first used a stone as a bludgeon?”]

We defined learning. We established why it’s important. It follows that, given its importance and our finite time, that faster is better (holding quality constant). We laid all this out but did not talk about how.

How do we learn?

Well, the how is critical because it’s the advice for new grads follows very naturally from the how.

We learn from risk. From bearing the cost of trial-and-error. School trains us to appease. Generally, the expedient way for a student to meet there 2 biggest goals, namely to get good grades while minimizing the teacher’s interference in the student’s affairs, is to flatter whatever dogmatic attachments the teacher harbors.

In elementary school, the answer the teacher wants and the right answer are aligned. Spelling, remedial comprehension, basic math operations. As children mature, the classes become more subjective. Risk becomes more inconvenient for the student as there is no marginal payoff vs reciting the “acceptable” answer since the ceiling is an A+ and is designed to be accessible. In real life, separation requires a combination of excellence and risk. I suspect many reading this will find it self-evident from experience that good grades had such steep conditions.

When you graduate, you want to optimize for learning and learning velocity. You want to prioritize for:

  1. Risk and accountability
  2. Working with exceptional people

The problem is these are not always straightforward to evaluate from the outside and the shortcuts that help evaluate don’t often work where you want them to.

Risk and accountability

You want responsibility quickly. In fact, this single fact was a major factor in choosing SIG over a bank when I graduated, despite far less up front pay. I wanted acceleration not a tantalizing y-intercept.

But zooming out a bit, I wanted trading more than banking because the whole field meant the chance to sink or swim sooner. I can’t explain it better than Paul Graham does in his classic essay How To Make Wealth:

Economically, you can think of a startup as a way to compress your whole working life into a few years. Instead of working at a low intensity for forty years, you work as hard as you possibly can for four. This pays especially well in technology, where you earn a premium for working fast…

Companies are not set up to reward people who want to do this. You can’t go to your boss and say, I’d like to start working ten times as hard, so will you please pay me ten times as much? For one thing, the official fiction is that you are already working as hard as you can. But a more serious problem is that the company has no way of measuring the value of your work.

Trading is not technology, but it’s similar in that you aren’t spending your time stapling and copying. But say you are not in trading or a start-up, how fast do you get to be at a client dinner or? How fast do you get to make decisions that impact the company’s p/l by choosing from a set of possibilities where there is a dispersion of value over the replacement or default decision? You want to ask the interviewer these questions, although I might try being more indirect unless you think impatience will reflect well.

Tactically, this means either trying to work for a smaller company, a startup in the limit case, or a company whose functional work teams are lean such that its members’ contributions are critical. Whatever the equivalent of a pod is in the industry you are entertaining.

Finally, there’s the canonical case in trading of someone getting fired and the boss tapping the trading assistant who is most familiar with the book to step up to manage the position. If you are talented and hang around the rim of any position where talent matters, you’re a 1 night away from all the responsibility you can handle.

My favorite such story is my friend Tony thrust into hosting Around The Horn for the first time when Max Kellerman suddenly left the show. That day was the start of an almost unheard-of 21-year run as an ESPN host. Talk about being thrown into the fire, that was the day after the Janet Jackson nipplegate Super Bowl.

Working with exceptional people

This one is hard to judge from a few rounds of interviews. The more experience you have with people, the better your judgment gets. You’ve seen how first impressions cash out, you recognize red flags, and the reps build intuition. But job-matching is naturally adversarial since the stakes are high. You’re trying to find who you’ll apprentice under, and that person who emerges as your eventual mentor might never have been in the room during interviews.

You’ll need to reach for heuristics. Unfortunately, the good ones are weak and the convenient ones are broken. Credentialism has some signal. I don’t think I’ve ever met an MIT grad who wasn’t smarter than me. But the error bars on the signal path from even honest credentials to efficacy are wide. The Stanford PhD who can’t reason out loud and the state-school kid who dismantles your argument in five minutes are data points your priors lack.

In fact, the state-school stud example is a common version of the credential trap. Berkson’s paradox tells us that inside any selected pool, the visible signals stop telling you what you think they tell you. If you see a short kid start on one of the best varsity basketball teams in the state, get ready to watch an absolute savage. The population correlation will correctly predict that taller people are better basketball players, but when you restrict the range to people already on a basketball team, the correlation loses predictive value and can even invert at the extreme. The Taleb version of this idea is that you don’t want a surgeon who looks like someone who plays a surgeon on TV. I say it a lot, but once you are familiar with Berkson’s, you see it everywhere. When you are in a wicked info landscape knowing these little anomalies can counteract the System 1 snap judgements trained on population-level observation.

Let’s move to company reputation. Reputation, the literal outside view, is a convenient heuristic. With enough samples can sketch a reasonable portrayal of a company. But it won’t work where my first piece of advice sends you — (not AI dash, sigh) to a lean team where your contribution is critical. Not enough samples. You’d be lucky to find even one. The places everyone has opinions about are, almost by definition, big and legible ones, therefore the least likely to give you the responsibility you actually want.

Unfortunately, there’s no shortcut to spotting exceptional colleagues. It is the bane of employers and job-seekers alike and it’s not for lack of effort. There is tremendous leverage not only in hiring well, but in the spirit of all this advice, to learning extremely fast if you find the right mentor.

An exception

We’re giving preference to going to a small company where you are pressured to learn fast and compress your timeline. But there’s a specific class of bigger institutions that earns an exemption. These are the places that have managed to formalize their the hard-won, domain-specific practical wisdom, or metis, that usually lives only within individuals. The default in companies, especially those that have a star culture, is that knowledge stays tacit and exits when good people leave.

Most organizations cannot or will not invest in the preservation and transfer of knowledge because it’s expensive. Some companies may see training as a box to check, while those with a long-term view will see it as an investment in a compounding edge. If you are talking to a firm in the second category, you are at the doorstep of rapid learning even if the org chart is a pyramid.

A few concrete examples of orgs known for their training:

  • Navy SEALs are experts in decentralized command under pressure. They fuse a culture of risk assessment and extreme preparation. The government spares no expense in manufacturing these soldiers. (My favorite book during every man’s signature special ops rabbit hole is Lone Survivor which my older kid also loved.)
  • SIG and Jane Street fancy themselves the SEALs of discretionary and quant trading, respectively.
  • Goldman is in the fancy client business. I imagine it’s hard not to walk away without some durable closing skills and a smidge of dark arts.
  • P&G built the academy that trained a generation of CMOs in brand management with their alumni in leadership roles across hundreds of giant consumer companies. The playbook for selling a commoditized product existed well before the era of digital marketing.
  • Finally, Disney Institute and Chick-fil-A are widely considered the template for customer service.

Blood from a stone

It can’t be overemphasized. The purpose of a new grad’s job is rapid learning. Hopefully, in the field they want to be in (although the messy process of learning can also mean self-discovery and detours which are fine if not expected). But in the very real possibility that the field isn’t for them, it’s more important that the rapid learning is for skills that mesh with their talents and can find purpose in whatever direction their careers evolve.

Since it’s unlikely that one’s first job is their last, let me offer a final bit of advice. It’s time to change roles or companies once you feel your learning rate slow to a crawl. When professional gains feel like blood from a stone, it’s time to poke around. Explore. Maybe develop new skills at night while you bide your time. There’s even a chance these explorations rejuvenate your current role as AI has done for many.

I mention this because there can be a disconnect between learning rate and how things are currently going for you. This is definitely a trap. Results are a lagging indicator of effective learning. The cost of slow growth shows up in the future, delayed by the comfortable harvest seeded by your previous high learning rate.

I leave that as a warning. I will tell my kids the same.

Wrapping up

  • Optimize for learning rate. Not pay, not prestige, not the y-intercept. You want acceleration.
  • Actual learning requires risk and accountability
  • When you find an exceptional colleague, help them and if you can learn from them you’ll compress time
  • If opting for a big company, focus on those who make serious investments in training that will serve your career especially since you are unlikley to stay at the first big company you work for
  • When the learning becomes blood from a stone, you need to make a change. Your own stagnation follows on a lag.

When in doubt, ask yourself where you will learn the fastest.

stacking carry: an inflation hedge you get paid to own

US bond yields are rising as inflation re-enters the conversation. The 10-year yield is up to 4.65% and 30-year bonds have just crossed 5%, a nearly 20-year high.

This isn’t surprising. 6 weeks ago, in Trading As A Sudoku Puzzle With Prices As The Given Numbers, I talked about how 1-year gasoline futures were trading at a 1/3 discount to prompt pricing, but if gasoline prices remain high, this will roll up. If spot prices stay high for a year, those back-month futures will converge to current prices. Even though energy is only about 5% of CPI, the size of such a sustained move would easily transmit 1.5% to inflation indices and that is just due to direct energy effects and ignoring indirect effects on food, construction, and transport.

We’ll switch the conversation to crude oil just because it’s more widely tracked and the specifics of the contracts aren’t critical to where we’re going. Prompt oil is roughly in the same place vs 7 weeks ago, but the contract that was 12-months out and is now 11-months out has rolled up >6%. Meanwhile, another month of sustained high oil prices has pushed the 10-year yield up 30 bps from 4.3% to 4.6% with IEF price returning about -1.6% a bit better than what’s expected by its duration.*

*There’s some leeway since I’m using an index for the yield which may have a different set of weighted maturities than IEF holds. Also, IEF total return is closer to -1.1% because you earn interest for 7 weeks.

So far, so good. The reaction function in bonds makes sense. But my Sudoku post claimed that an inflation-induced yield bump would transmit to real equity risk premiums. In other words, I would expect equities to sell off with bonds, or heck, at least not have such a sharp rally.

This is not quite the puzzle it appears to be. The equity exuberance is actually quite limited if you look under the hood of the index.

From Shannon’s substack:

The internals are doing something the people who watch this for a living have never seen. The S&P is up 4.2% month-to-date with 209 stocks up and 295 down. The NASDAQ is up 8% month-to-date on a near-even split (51 up, 50 down). The index is 9% above its 50-day moving average while only roughly half the components are above their own 50-day; at that distance you’d normally expect 80% breadth. Four days running, more S&P stocks hit new 52-week lows than 52-week highs, with the index at all-time highs and up 30% year over year. Yesterday 9% of the index hit new lows. None of this happens together in a healthy tape.

I’ve noticed many market people interpret these “internals” as bearish. I’m not sure this is bearish for the index. It just is. A few companies are eating everything else. We get it. At this point, the low cross-correlation of the components is common knowledge (isn’t this what managers call a “stock pickers market”?).

Rather than use the term “bearish” which has a predictive slant I can’t justify, we can just accept that the sustained oil price, inflation jitters, and rise in yields are being reflected in prices broadly. SMH (semis ETF) is near 1-year highs while XHB (homebuilders) are near one-year lows.

The AI story is in a parallel vacuum, indifferent to relics like discount rates or identities such as spending = income, but stocks overall are not being indiscriminantly bid. SPY has returned nearly 2x RSP, the equal-weighted SP500 index, over the past year. So the loving arms of our cap-weighted benchmarks hold us tight, shielding our eyes from the turmoil within. Trepidation over supply-side inflation is confirmed by bond and non-AI stocks alike.

Concerned with inflation, I dust off some old posts, like What I Learned About TIPs which I wrote when I bought when breakevens shrunk to about 2.2% (green box).

(When breakevens are skinny, TIPs are relatively cheap compared to nominal bonds, and when they are fat, they are relatively expensive. The way to think of that is if you buy TIPs at say 2% breakevens, then you are better off with the TIPs if CPI realizes more than 2% and vice versa.)

Breakevens are currently matching 3-year highs so TIPs don’t look attractive on a relative basis, but that’s only one lens. The real driver of my decision to buy TIPs in Oct 2023 was the absolute real rate which was ~2.45% which still stands as the peak for most investors under age 40’s working life.

Remember that’s 245 bps of return above inflation for no risk and if you hold them in an IRA, no tax drag. Historically speaking, equity real returns have been in the range of 3-6%, but recent years have been quite a run of heads. Whether the coin is biased now is a question for someone smarter than I. But I digress.

The point is I’ve started once again to consider inflation-aware trades. 10-year TIPs don’t stand out as a bargain relative to nominal bonds. I’m wary on gold and silver because of how well they’ve performed recently, but also historically, they have not been great to own when real rates increase and we can see from the absolute TIPs rate that, despite breakevens not breaking out, real rates are crawling higher, approaching an 18-month high.

So I dust off yet another post, this one from 2 years ago: Inflation Replicator. I show how a portfolio of oil futures plus nominal bonds mimics the behavior of inflation-indexed bonds like TIPs. I constructed it in Composer using USL, which holds a strip of oil futures maturing within the next 12-months, plus TLH, a bond ETF holding bonds with 10-20 year maturities. The portfolio is inverse-vol weighted, rebalanced quarterly.

This is the out-of-sample performance since I published the post (green line).

That portfolio is a set-and-forget inflation hedge if you don’t like TIPs.

[Speaking of “tips”, here’s a general one. If you have a portfolio that rebalances, it is often selling winners to re-invest in losers. This keeps you diversified and avoids the volatility tax that comes from concentration, but it’s not tax-friendly unless you do it in a sheltered account. To do it in a regular account, you can consider a tax-loss overlay where instead of buying more of the losing position, you actually sell the losing position and another ETF that has a highly correlated exposure. So, for example, if TLH is the losing side and you need to add more on the rebalance, you actually tax-loss harvest the TLH and replace it with TLT length. It’s a similar exposure, but you can now use the TLH capital loss to offset the gain on the USL win you trimmed.]

The specific inflation replicator I composed was TLH + USL. But if we abstract it to “bonds + oil”, it invites us to think about risk premia that exist in both asset classes in the current market.

In the remainder of this post, I’ll narrate layering a couple of edges onto a core portfolio idea. By following along, you’ll get concrete ideas for measuring and managing risk and open your mind to the different Legos available to build the portfolio and ultimately express the trade while targeting the carry embedded in the asset’s pricing complex.

Inflation Replicator with positive carry

Let’s talk about our baseline exposures: oil + bonds

Instead of building the inflation replicator portfolio with the USL ETF, we want to isolate a carry-rich version of “oil”.

The oil leg

As I write on 5/20/26, the prompt WTI future, CLM6 (expires in May), is $98.

CLZ6, expiring in November, is $81.75.

If the spot oil market is unchanged over the next 6 months, CLZ6 will “roll up” nearly 17% (~34% annualized).

The bond leg

Long TLT shares. You collect the ~5% annual yield as carry. That’s the simplest expression and what we’ll size against.

Reiterating the core idea of the inflation-protected bond we are creating

We are pairing oil and bonds together because high oil prices are a major driver of inflation and the accompanying weakness in bonds. In other words, the bonds and the oil hedge each other if we own both.

They are coupled antagonistically. Look at the correlation of TLT (longer-dated bond ETF) and USO, which holds prompt WTI futures.

moontower.ai

Before the war, the rolling 21-day correlation of returns between TLT and USO ranged from about zero to -.50, spending the bulk of the time between 0 and -.25.

Since the war, the correlation range abruptly shifted lower, recovered a bit and has now collapsed to -.75.

💡Does it matter that we are comparing TLT with prompt WTI via USO when we want to express crude length with the deferred Z26 contract? The vol of the two contracts is very different, which matters for sizing reasons and would show up in the beta, which is vol ratio * correlation. But correlation alone is still tight across the futures strip with M1 to M6 easily above 0.90. It’s safe enough to infer the correlation of TLT to Z6 futures from its relationship with USO.

You will see how the inflation replicator portfolio benefits from the negative correlation when we get to sizing. Understanding the correlation range will also be key, as it’s a critical input to risk management.

Sizing the core portfolio

We begin with a risk target expressed as a fraction of a portfolio. We’ll choose $100k of annualized volatility allocated to this trade. Feel free to pick your own number, the method is what matters.

A $100k annual vol target is easier to reason about if I convert it to a daily number, because daily P&L swings are what I actually watch on the screen. Annual vol scales with the square root of time, so:

$6,300 of daily swings is for the portfolio of oil futures + TLT. We need to size the individual legs of the trade.

Step 1: convert each leg’s vol to a daily number

Again, we are converting annual vols to daily by dividing by √252

CLZ6 has 43% implied vol → daily vol ≈ 2.71%

TLT has 11.5% implied vol → daily vol ≈ 0.72%

Oil is about 3.7x as volatile as TLT on a same-dollar basis.

Step 2: inverse-vol weight the two legs

Inverse-vol weighting means I want each leg to contribute the same daily dollar volatility to the portfolio. Not the same notional, the same risk. The high-vol leg (oil) gets less notional, the low-vol leg (bonds) gets more, until they pull equal weight in risk terms.

Mechanically:

The daily dollar vol due to either asset should be equal. We’ll set that dollar vol equal to S.

Step 3: solve for the portfolio vol as a function of S and correlation

This is the two-asset portfolio variance formula:

 

The w’s are dollar weights, the vols are in daily percent, ρ is correlation.

Inverse-vol weighting forces w₁σ₁ = w₂σ₂ = S, therefore every term becomes a multiple of S²:

 

That’s the engine. Portfolio daily $ vol is just the per-leg $ vol scaled by √(2(1+ρ)).

Note how correlation has such a large impact on the portfolio vol. At today’s ρ = −0.75, the multiplier √(2(1−0.75)) = √0.5 ≈ 0.71. The portfolio is less volatile than a single leg.

Step 4: invert to find the leg size

I want σ_p = $6,300. Solving the formula above for S gives S = $6,300 ÷ √0.5 ≈ $8,900. So each leg should carry about $8,900 of daily dollar vol.

Convert that back to notional: oil notional = S ÷ daily oil vol = $8,900 ÷ 2.71% ≈ $328,000.

  • CLZ6 is $81.75 and each contract is 1,000 barrels, so one contract is ~$81,750 of notional. $328,000 ÷ $81,750 ≈ 4 contracts.
  • TLT is .72% daily vol, so we need $8,858/.72% or ~ $1.22mm of notional or about 14,500 shares because TLT is $84

[$8,858 instead of the $8,900 we solved for comes the fact that we need 4 contracts that are not divisible any further. Note how the bond notional is ~3.7x the oil notional, exactly the inverse of the vol ratio.]

And the resulting portfolio daily vol at ρ = −0.75 is σ_p = $8,858 × √0.5 ≈ $6,263. Right on our $6,300 daily risk target, which corresponds to $100k of annual vol.

The beauty and danger of correlation

Let’s appreciate what’s happening here by considering monthly risk and reward.

Let’s start with risk.

Scale daily risk to monthly:

$6,300 *√(252/12) = $28,870

Now for the expected reward.

Oil: 2.5% roll up * $327,000 notional = $8,175

TLT: 5% yield * $1.22mm / 12 months = $5,083

Total expected return = $13,258

Monthly sharpe ratio = $13,258/$28,870 = .46

Annualize the SR:

.46 * √12 = 1.59

This is possible because we get to be long quite a bit of assets in notional terms, but the volatility of the portfolio is small.

The reason it’s so small is that the correlation is very negative.

But ρ = −0.75 because the war pushing oil up is adding a risk premium to bonds (ie pushing their price lower).

To understand the risk, we must stress-test correlation. We fix S and vary ρ.

[Risk should really be treated like a matrix since changes in the correlation will coincide with the vol of the legs moving, thus changing the vol ratio between them. For example, if the war relaxes and the correlation heads back towards 0, oil prices likely fall, bonds likely rally. That’s ambiguous for the p/l, but since oil’s vol is the one that’s more stretched from “normal” you are underweight the falling asset which is good. However, the increased correlation means total portfolio risk is more than you intended]

Your portfolio risk doubles if corr goes back to 0.

Juicing the bond leg with options

So far the bond leg is plain-vanilla long TLT shares earning the ~5% yield. But given the sell-off and inflation fears, the bond option market is also offering risk premia as vols have increased and put skew has steepened.

Let’s talk about the vol first.

VRP

As I write on 5/20/26, the ATM 1-month put is around $1.20, corresponding to 11.5% IV. TLT’s realized vol has been running below its implied. 1m realized vol is ~8%, 1-week rv is closer to 9% and median 1-month rv for the past year is about 10.5%.

Call it a 15% vol risk premia:

  • Put premium: $1.20/share
  • Fair value: $1.20 ÷ 1.15 ≈ $1.043/share
  • VRP edge: $1.20 − $1.043 ≈ $0.157/share, or 15.7 cents per share

The practitioner’s way to carry that number in your head is per contract. Each contract is 100 shares, so the VRP per contract is $0.1565 × 100 = $15.65 per contract per month.

The bond leg’s delta target was the equivalent of +14,556 shares of TLT. An ATM put has a delta of about −0.50, so selling one put gives you +0.50 deltas per share, or +50 deltas per contract (100 shares × 0.50). To replicate the share position’s delta: contracts = 14,556 deltas ÷ 50 deltas/contract ≈ 291 contracts.

291 × $15.65 ≈ $4,555 per month, or ≈ $54,700 annualized.

If you sell ATM puts to express the same long-delta exposure. You collect the put premium, and the portion of that premium above fair value is vol risk premia stacked on top of the yield carry.

💡It’s never that simple when it comes to options. The yield carry is the yield * notional but as TLT moves around, you are short gamma so as the stock falls you are longer TLT and as it goes up, you become less long TLT, so the yield due to bond income is a moving target.

Be careful. 291 contracts on an $84 stock is $2.44mm of gross notional, even if it’s still $1.22mm share-equivalent notional. The local delta exposure is identical, but by swapping the expression to pick up VRP we added non-linear risk to the position.

Skew

TLT’s 1-month risk reversal is at the 94th percentile of the trailing year. The put skew is rich, call skew is depressed.

montower.ai skew percentiles (puts on x-axis, calls on y-axis)
moontower.ai

You can express the delta by selling OTM puts, which will make the risk non-linearities even more concave. You can also sell put/buy call on risk reversals to take advantage of the stretched skew in both directions. All of this is changing the shape of the p/l and risks dramatically. The best way to get your arms around it is to construct a matrix of scenarios.

Oil options

The bond leg harvests rich skew by selling puts but the oil leg can do the same thing in the opposite direction.

Oil call skew has a war premium. That makes a call spread an attractive way to express the long oil leg: buy a closer-to-the-money call and sell a further-OTM call at a stretched IV against it, financing part of your long with the fat skew you’re selling.

For example, instead of buying 4 Z26 futures, you could buy the Z26 88/98 call spread. With the underlying at $81.75 this OTM structure costs ~ $2.35. It has a .12 delta, so to get 4 contracts worth, you’d need to buy ~33 call spreads (4/.12).

You’re long the rollup-and-supply-scare upside, but you’ve capped your gain to $7.65 (about 3.2-1 odds on your premium), but your downside is limited to the debit if Hormuz de-escalates and oil pukes.

Trade management

It’s well understood that when it comes to options your risk is changing as assets move around, as time passes, and as implied vol fluctuates.

A more subtle risk is how your exposure changes on the oil leg even without options. The oil future becomes more volatile it approaches maturity ages. The 6-month oil future currently has a 43% implied vol but the near-dated future can be twice the vol in times of stress. So even if nothing moves, the oil leg’s daily dollar vol creeps up over the life of the trade. This might be partially mitigated by the roll-up amount becoming steeper as you approach the front of the curve.

The 1-month rollup from M2 to M1 is twice as steep as the 1-month rollup from M6 to M5.

CL futures via TradingView

 

The good news: the same risk framework that sized the trade also manages it. Re-run σ_p = S·√(2(1+ρ)) with fresh inputs whenever the market moves:

  • Oil vol rose? Each leg’s S is no longer balanced. Trim oil contracts (or tighten the option overlay) and add bonds to re-equalize the legs and pull portfolio vol back to the $6,300 daily target.
  • Correlation drifting toward zero? The shock table prescribes how to proportionally hold both legs to maintain the vol target.
  • If you use options and your total risk or relative leg risks get out of tolerance bands, you can reassess to see if you should roll, add, or even close.

Because the trade is a living position, you may want to treat the target risk as an upper bound, and initiate the trade at smaller sizing giving you wiggle room to rebalance less often.

A summary of stacked edges

The bond leg is long carry because the position has a net long delta (yield) and short rich puts (VRP).

The oil leg is long carry (rollup) and short rich calls (skew).

You’ve taken a simple “buy oil, buy bonds” inflation replicator and layered distinct edges onto it, each one sourced from a risk premium in the pricing complex:

  1. Oil rollup carry (term structure)
  2. Bond yield carry
  3. Bond VRP + put skew
  4. Oil call skew

On the carry side, you are monitoring VRPs, term structure, and coupons, while on the risk side you are monitoring the volatility of the legs as well as the correlation which has a major impact on the portfolio risk.

How big a portfolio does this need?

I sized everything to $100k of annual vol, but I never said what size account sits behind this trade. Vol targets don’t specify a portfolio on their own — they specify a portfolio once you decide what fraction of your risk budget the trade gets. If you want this to be a 10% vol sleeve, you’re implicitly running it against a $1mm book. A 5% sleeve implies $2mm.

You’ll immediately notice a problem if you consider the 10% / $1mm case. The bond leg alone is $1.22mm of TLT shares, which exceeds the entire account. You can’t fund it with cash, you need leverage. Futures are inherently levered as you only need to post initial and possibly variation margin. For the equity portion, portfolio margin can allow you to post even less than a 50% haircut.

But leverage introduces path risk. Your position is changing with market conditions, especially if you use options. But this portfolio sizing is resting on a large position in a low-vol asset as well as a negative correlation. The simplest way to appreciate the risk is to notice that a mere $100k of annual vol rests on ~$1.5mm gross exposure. If you run this portfolio at $100k annual vol with only a $1mm account, you are managing both risk and margin closely.

Recall the portfolio expected Sharpe was 1.59. So for $100k annual vol, we expect $159k in profits or 15.9% on a $1mm account. The expected return halves to ~8% if you run it in a $2mm account.

The best but most complicated choice is to run a strategy like this in a diversified account where the other moving parts interact with the portfolio margining computations such that the required haircut is small and therefore efficient.

Let’s leave it there for today.