become an option mixologist

To piggyback off David Epstein’s explanation of chunking, I’ve discussed the technique several times in my writing in the context of options. I use the chess player’s word for it (although I’m not a chess player): dissection.

These articles give concrete examples:

The second one links to a video where you can follow along on an example.

At first, you consciously look for groups or patterns that compress a theme, but with practice this becomes automatic. You can’t help but see the pattern.

Like the sports examples, an experienced trader will be able to pull the trigger faster than slavish processing would allow. The shortcuts become part of their wiring. You could see this in an open outcry trading pit or even amongst the best mock trading students back in the old floor days. That ability to say “sold” or “buy’em” faster than a large group of competitive traders because you saw the arb line up is happening at a subconcious pattern level. You make the trade and working out the particulars of the “why” while the instructor is still in the act of halting the the class to ask why you made the trade. I don’t know how it works but my pop science guess is that your synapses which have been strenghtened along specific pathways are a step ahead of your explicit reasoning.

Dissection is a deliberate form of “chunking”. But if we zoom out a ring from the specifics of option structures to the parameters they express, there are only 3 we generally care about: volatility (or variance), skew, kurtosis. In stats terms, these map to the 2nd, 3rd, and 4th statistical moments of the distribution.

There’s a vanna-vega-volga model sometimes referred to as “the cost of gammas” framework which actually formalizes this idea by mapping the parameters to their costs.

Volatility is represented by the cost of the straddle.

Skew is represented by the cost of a risk reversal.

Kurtosis is represented by the cost of a strangle.

These map to pertinent Greeks as well:

straddle → gamma

RR → vanna

strangle → volga

You pay IV premiums for all of these convexities. Vol risk premia for the straddle, you pay skew premiums for the ability to be long spot-vol correlation in the direction for which IV tends to rise as the market moves (so in SPY you pay a premium for the puts but in oil today you pay a premium for the calls), and finally, for volga, or “vol gamma” you pay an IV premium for wingy options.

To a beginner, the zoo of option structures is overwhelming. Seriously look at this page, the screenshot is only part of what I could capture:

It doesn’t even cover them all. There’s still jelly rolls, Christmas trees, rev/cons, diagonals, strips, “stupids”. I’m not kidding on that last one (it’s buying or selling a package of options in the same maturity but different strikes, so buying both the 700 and 650 puts as opposed to spreading them).

But if you understand that there are only 3 parameters we care about, then all of this collapses into a few themes. There’s a million different types of cocktails, but according to the mixologists at Death & Co there’s just key elements to the drink:

  1. alcohol (base)
  2. sugar (sweetener)
  3. acid (brightener)

If you prefer the cooking analogy, it’s salt, fat, acid, heat.

All recipes, whether in options, cuisine, music (there are thousands of chords but you can collapse to major/minor modified by dominant, sus, and add9) can be reduced to a few themes.

How does this help?

I’ll give you an example from our Discord this week.

Someone asked:

Anyone got any ideas for screening for good call spreads or put spreads to buy systematically in a potentially semi-automated way using moontower. A lot of the guidance I’ve read is ‘if you have a directional view’… well umm, I’m a ding dong with no directional ideas want something algorithmic.

I’m also a ding-dong, I just happen to understand that the price of option structures derives from the cost of our 3 friends: volatility, skew, and kurtosis.

This was my response:

What makes a vertical or debit spread generally cheap?

Low IV and high skew at the strike you are selling. So relatively cheap ATM/.25d call spread will have low IV and high call skew.

A relatively cheap OTM call spread could come from the IV being relatively low and the .25d call skew being low if that’s the long leg of the spread.

So here are a few suggestions…

  1. Sort for low IV percentile and high call skew for ATM to .25d call spreads or
  2. Sort for low IV percentile and low call skew if you want to buy an OTM call spread, meaning your buy leg is say .25d
  3. Use our Trade Ideas tab to look at names that score well on “Buy Vol” and then also sort by call skew in the table below!

You can also talk to the agent about building a prompt for this and then make it an Automation.

Our Trade Ideas algo scores names based on how they stack up to various preset trade themes (ie “buy vol”, “sell vol”, “long calendar”) according to their parameters and what signatures we look for. You simply add the column for 25d call skew which tells you the percentile, and using the logic from my answer, find names where the parameters present attractive spreads.

You had to understand that the price of the option structures map to these 3 themes in the first place and suddenly the zoo of possible option trades is massively reduced in dimensionality. It’s the progression from option bartender at your college party to option mixologist where you understand that all drinks are just a few flavors.

And just to address the Automations thing, we have a new feature in our tool. An example of one of mine where the agent emails me on a schedule when a name with a strong “Buy Vol” score’s strike vols are down and vice versa:

How I Teach Middle Schoolers To Build Stock Portfolios

If you construct a portfolio from 2 stocks and one is $100 and the other is $10, buying a share of each means the first will dominate your portfolio’s risk, assuming they have the same volatility.

If you have $100,000 to invest, you can balance the risk by equal-weighting the holdings: $50k into each stock. You buy 500 shares of A and 5,000 shares of B.

But what if they aren’t the same volatility?

Equal-weighting means the most volatile stocks determine performance. If your $100,000 is split equally between the 2 stocks and A moves 10% per day while B moves 1% per day, you aren’t diversified. Stock A will mostly determine your returns.

We can achieve more balance via equal-risk-weighting, which adjusts how many dollars go into each stock based on its volatility.

Weight each stock by 1/vol:

  • Stock A gets 1/10
  • Stock B gets 1/1.

Divide by the total (1/10 + 1 = 1.1) and you get about 9% in A and 91% in B. Stock A is 10x as risky, so it gets about 1/10th the dollars.

On $100,000 that’s roughly $9k of A and $91k of B, corresponding to

  • 91 shares of A
  • 9,100 shares of B

Compared to the equal-dollar portfolio, the equal-risk portfolio requires you’d sell about 409 shares of A and buy about 4,100 shares of B, moving roughly 41% of your total portfolio value from the jumpy stock to the calm one.

No masochism for the kids but in case you’re interested…

Equal risk weighting is the starting point for so-called risk parity weighting. The difference is that instead of only considering the volatility a holding adds to the portfolio, the correlation is considered. A stock highly correlated with the rest of your portfolio contributes a lot of risk, while an anti-correlated one does a better job diversifying and reducing total portfolio risk. The effect can be so strong that even a highly volatile but anti-correlated stock can reduce total risk.

Computing a correlation-aware risk contribution requires a full covariance matrix and an optimizer — i.e., a guess-and-test calculator — to find the portfolio weights, since there’s no closed-form solution. If the kids can grok equal vol-weighting I feel like I’ve done my job, and they can discover risk parity on their own if they’re so inclined.)

Your own Portfolio HQ Spreadsheet

This workbook is designed to organize and monitor your first portfolio.

⏬ Download

The sheet is view-only. Select “duplicate” from the file menu to get your own copy.

In this video, I show you how to use the sheet and talk about the Investment “lab” we did this week.

investing orbits

Here’s a summer reading book rec for investors:

My wife and I are both reading this. It’s laugh-out-loud funny. Gary is an excellent writer. The novel is written from the point of view of an elite school’s endowment CIO. It presents as a series of meetings with prospective managers, deals with politics within the endowment but also with the external culture of the investing world. If you are in finance, Gary’s sharp eye will delight you til no end.

I’m less than halfway through it and already I can’t recommend it enough. It was recommended to me by an allocator (thanks Tom!) and I saw in a recent Byrne Hobart letter that one of Byrne’s friends physically accosted him for not having read this book yet.

You can see Matt Levine’s endorsement in the screenshot. I wouldn’t have articulated what Matt wrote, but once he said it, I noticed that’s the exact feeling I get reading it.

The CIO’s banter, verbal chess, and inner monologue reveal a fox-like savvy honed by years of battle with both the market and the managers who make convincing cases for how they’ve mastered them. It gave me a tremendous appreciation for the difficulty of the job. If you are not a professional investor and have confused the most generous market run in anyone’s living memory for your own brilliance, then considering the CIO’s constraints will update your context for the pro version.

I found this recently reinforced by Jeremy Giffon in this terrific interview on ILTB.

Patrick: You have this funny view that the whole myth of how difficult it is to beat the market, however you want to define the market, is wrong. I’m curious for you to expound on that. That seems to have become, post-Jack Bogle, one of the deeply held truths of the market is that it’s extraordinarily difficult to beat the market, so you shouldn’t even try. You should just opt out of the battle. I think you have a very different view on this.

JeremyBuffett and Munger were my main teachers on investing. Buffett says that he wants his estate outside of Berkshire to be put in the S&P. That’s his advice to the general public. People take that to say that Buffett’s saying you can’t beat the market. I don’t think that’s what he’s saying. I think he’s saying for the average person, you shouldn’t try and beat the market. Implicit in that statement is leaving out any sort of active investor. Maybe the anecdotal side would be Buffett saying you should put all your money into the S&P. That’s the most rational thing you should do. On the other side is the sort of empirical argument, which is, look, most professionals don’t even beat the market after fees. This is this one-two punch of — the godfather of investing says, don’t try. Seemingly the smartest people with the best incentives in the world can’t do it.

And then the other thing is, for a professional manager — and this is sort of the paradox with the Buffett thing — it is really hard to beat the market because you have all these other factors that the average person doesn’t have. And this is the Peter Lynch argument — and increasingly I think Peter Lynch was a genius about this — which is that, yeah, when you’re a professional manager, by and large, you have all these mandates, you’re running a business, you have customers that you need to keep happy. It’s more difficult for the professional money manager to beat the market than the average amateur.


This is from Mandy Xu at the CBOE this week:

The outperformance of small-caps is a sign that the equity rally – which has long been dominated by the mega-cap Tech names – is starting to broaden out. In fact, over the past month, Tech has been the worst performing sector (-10%) while YTD laggards such as Healthcare and Financials have been the best performing (+12% and +8%, respectively). The calm at the index level (SPX Index -1.7% over the past month) belies these large rotations underneath the surface. This is why single stock volatility has been so elevated, even as the VIX® Index has fallen. The spread between the two, as measured by the VIXEQSM-VIX Index spread, widened to an all-time high of 31% last week.

If the single stock volatility is high relative to the index volatility, that’s another way to say the realized correlation between the stocks is very low. The index is dampening volatility because it’s acting well-diversified. A so-called stock-pickers market.

There’s so much violence under the surface. A momentum rotor whirring to give different categories an unpredictable spotlight before abruptly re-targeting.

I’m going to think aloud here a bit.

On the one hand, the momentum rotor feels like a market technicals concept. It’s the signature of flows and liquidity reaction functions. The intent of the orders that generate these flows might have a fundamental thesis behind them. In an investing mind. The trading world is indifferent to the ultimate intent but seeks to collect a service fee by spreading the acute dollar pressure in one part of the investing crust to another part of the surface.

From this perspective, the marginal price is set by an active investor. Perhaps the cumulative orders of levered pods.

At the same time, we hear of the “passive” bid. The Trump accounts and their monogamy to the SP500 (for the moment anyway) being yet one more increment to the bid.

If passive is the marginal price setter, I’d actually expect correlations to be structurally increasing. Not only do they seem to be structurally falling, they are conspicuously dormant at today’s historical lows.

I’m not sure the best way to reconcile these arguments. Is it an artifact of observation at a short time scale (rotor flows) vs a longer time scale (a slice of S in the GDP identity is pro-rata routed to the SP500 as long as the economy grows)? It’s reminiscent of the Earth’s dual rotation, where the planet spins on its own axis while orbiting the sun. The momentum rotor is called a “day” and the steady levitation of valuation comes from the passage of the “years”.

Regardless of the reconciliation of orbits or lack thereof, I am fractured by an ongoing dissonance:

I don’t discuss any of this in the Investment Beginnings Course!

It’s easy to anticipate a commoner’s consolation. “Kris, you are right to be teaching the textbook basics; we want the kids to learn investing, not gambling.” But it does feel quaint and too convenient to not address the marginal price setter. Buffett does so in a particularly striking way based on Graham’s allegory:

He said that you should imagine market quotations as coming from a remarkably accommodating fellow named Mr. Market who is your partner in a private business. Without fail, Mr. Market appears daily and names a price at which he will either buy your interest or sell you his.

Even though the business that the two of you own may have economic characteristics that are stable, Mr. Market’s quotations will be anything but. For, sad to say, the poor fellow has incurable emotional problems. At times he feels euphoric and can see only the favorable factors affecting the business. When in that mood, he names a very high buy-sell price because he fears that you will snap up his interest and rob him of imminent gains. At other times he is depressed and can see nothing but trouble ahead for both the business and the world. On these occasions he will name a very low price, since he is terrified that you will unload your interest on him…

Mr. Market has another endearing characteristic: He doesn’t mind being ignored. If his quotation is uninteresting to you today, he will be back with a new one tomorrow. Transactions are strictly at your option. Under these conditions, the more manic-depressive his behavior, the better for you.

Mr. Market is there to serve you, not to guide you.

Yet, I have my humble reservations about Buffet’s view. It’s not that I think it’s wrong, it’s that it leaves you in a quandary about a critical aspect of decision-making. How do you weigh information when forming an opinion?! A strict reading of Buffet is that Mr. Market is emotional and irrational. But traders are taught to respect bids and offers. They are made with real money in proportion to conviction. It’s exactly why we say betting is a tax on bullshit. The essence of trading decisions is how you form priors and then Bayesian update. You can’t ignore bids and offers if you think they contain information (and you certainly would care about if the bids and offers are forced or “uneconomic”).

[The maximalist Buffet view is that “short-term”, an admittedly poorly defined descriptor, price behavior contains no information. I’m not actually opposed to this possibility under some conditions but it’s obviously not universally true. The price signals from shortages and surpluses in the physical world matter. It’s the entire basis of capitalism. Insofar as share prices are an inference on the supply and demand of the physical world, we should not ignore their deltas. But the amplification embedded in the math of capitalizing those inferences into a multiple leaves a lot of room for accepting and refuting its justifications.]

Circling back to what I teach the kids in the future or possible course edits might be to discuss macro simply in terms of Kalecki-Levy type accounting identities. They aren’t predictive but they are explanatory. Every liability is someone else’s asset. So if the G deficit spends, the private sector savings mechanically increase (I need to review the framework, to be accurate in teaching it, but you get the gist). Some of that S will be siphoned into stocks, creating structural demand to be weighed against the arrival of issuance (ie supply).

From that foundation, one can see the movement of the index of all corporate shares as one orbit, and the micro discernment of relative value underneath being the subject of traditional valuation canon, while the trading/gambling science informing the physical “equations” that govern the sector rotor.

I stuck with physics in adherence to the orbital analogy but we all know investing is biology.

But I’ll wrap with a quote from my article about why it feels like astrology (this remains the most widely read post in moontower history):

In a recent interview on Corey Hoffstein’s Flirting With Models, volatility manager Cem Karsan explains:

In the very long term, all that matters is cash flows. At some point you’re gonna have a liquidity crisis and when the liquidity is not available, companies have to create their own liquidity and that’s where fundamentals matter…they matter, to the extent that they are necessary for purchasing their own stock or buying other companies.

I’ve used this analogy before, it’s kind of hokey, but I can’t think of a better one. If you’re on an airplane, 30,000 feet off the ground, that 30,000 feet off the ground is the valuation gap. Valuations are really high, but those engines are firing. Are you worried up in that plane about the valuations or are you worried about the speed and trajectory of where you’re going, based on the engines, based on the flows? The flows are what matter for where you’re going.

But when all of a sudden those engines go off, how far off the ground you are is all that matters. And so, [valuation] is more of a risk management tool, and ultimately it really matters when you have a liquidity crisis. It also matters if rates were to go back to 8, 9, 10%. Something crazy again, where nobody can borrow money, and there is no liquidity. Cash flows are all that matters again and we have a world where fundamentals are all that matters. So I want to be clear. It’s not that fundamentals don’t matter at all, it’s that they don’t matter in a world of massive liquidity.

I’m not naive enough to envision a unifying theory of investing, but teaching the class does motivate an impulse to do better than the textbook in tying things together in a way that is not just correct-ish but useful and relevant. And respectful to preteens and teens’ intellects, for whom education is increasingly patronizing.

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?

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

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.

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.

face-ripper

If you reside in the quark-sized intersection of people who read this letter but don’t follow the market, I’m informing you that shares of corporations are up sharply in the past 5 weeks.

The magnitude and speed of the rally have been “hellacious” to use a mentor’s favorite way to describe the face-ripping bear market rallies. Not that this is a bear market rally. As you know, bears are extinct and all the degeneracy you see is their normal diet flourishing without a natural predator.

Now, about that face-ripper…my turn to cherry-pick. It turns out selling calls that carry a high implied vol but were in the 0th percentile of skew wasn’t really “income”.

The green line is a portfolio of 75% SPY, 25% cash rebalanced monthly which is a more proper comparison to JEPI which sells OTM calls. Rough month for the home team.

If curious here is 75% SPY vs JEPI since it launched:

 

The rally has people confused. What about the war? What about oil? What the f is happening in this chart:

TradingView chart
Created with TradingView

It’s not even a single stock. It’s a sector. A sector with a big market cap already!

Two thoughts wash over me.

Thought 1: Is any of the news we see reliable? Do we have perceptions that are unlinked to reality, causing the market behavior to look so dissonant?

Thought 2: Horse said it best and this was only 2 weeks into the up-flush:

Let me save you some grief. Causality and stories are for historians, novelists, brand strategists, politicians, and grifters.

Traders are agnostic. Markets are Sudoku puzzles with prices in place of digits and risk/reward comes from the strain of contradiction. It can’t be otherwise. I saw Horse’s tweet after midnight when I couldn’t sleep so figured I’d pop off on why I agree.

Paradox of skill…the smarter markets are the more random it feels.

If lines to a game are well set you win some, you lose some and either way you pay the vig

The market not making “sense” …makes sense

Your making money shouldn’t depend on it making sense, because if it did, it would violate the idea that most people cannot make money trading (assuming the notion of sense was something shared)

This feels like some corollary to trading broadly…trading is about making money in the absence of knowing what is going to happen.

Trading is a practice that be adapted to any environment. Sometimes you inherit a departed trader’s position. You deal with it. You manage the risk. Your ability to do this shouldn’t depend on the market behaving according to your opinions.

I’m guessing that the needs-to-make-sense crowd sees the market like a physics or cause and effect problem rather than what it is. Positions and flows

(In the long run whatever that means it probably does make sense but nobody wants long run edge because it has long feedback loops and doesn’t maximize throughput of an actual edge like higher turnover, better sharp strats. But short term movements have no reason to make sense in any economic or textbook ways)

The market is just positions and flows.

Why does it go up? There’s a lot of savings in America seeking a return and not enough issuance that it desires to satisfy it.

I’ll use the overrated phrase “first principles” to describe what I think of the market when I zoom out:

Laws and governance matter because they modulate the rights of managers to extract, influence, and enhance both the paid and retained claims that shareholders own. And then those rules and incentives determine capital allocations to generate returns that hopefully justify spending our cells’ ATPs on these projects instead of killing each other in a world of scarcity. This is all crucially important and their fulfillment or lack thereof will make sense in the story of humanity. But they operate on a different time scale than trading or short-term returns.

The only way the short-term stuff will make any sense is from the vantage point of knowing what people’s orders are. But the reason their orders are what they are will remain opaque (excluding of course, forced or recipe-based strategies — which is why arb-minded traders think a lot about what Euan calls “inefficiencies” as opposed to risk-premia.)

Implications

1) Specialize

In a finance context, this is what I call “matching your strategy to your dashboard”. Warren Buffet doesn’t do technical analysis to evaluate a business. The input of charts is not relevant to what determines his outcomes. Likewise, a trader focused on an opening range breakouts strategy doesn’t care about free cash flow. If you listen to traders and investors talk, listen for how things that wouldn’t be critical metrics in their dashboard seep into their thesis.

Remember the Paul Slovic study where experienced horse handicappers are given a few pieces of data of their own choosing. Armed with their preferred data, they are able to not only make good bets, but also to be well-calibrated about their accuracy. Their confidence and accuracy were in agreement. However, as the bettors are given increasing amounts of data their accuracy falls, but their confidence shoots up. No bueno. Presumably, they were less experienced in weighing the additional data, which turned it into noise for their handicapping process.

Just to broaden this section for a moment. With the success of David Epstein’s Range and the internet’s vague references to the “world belongs to generalists”, it’s probably contrarian to recommend specialization. The generalists get all the attention. Who doesn’t want to be the macro Neo seeing through the matrix of green digital rain to pull money out of connections nobody else sees?

It’s not just macro. VCs are seen as generalist extraordinaires studying up on a wide spectrum of technologies. Just enough to “be dangerous” as the self-aware ones will admit. But the trader in me doesn’t see a group of people with any special ability to see the future (painting with a broad brush, if you’re a VC reading this, you’re special, don’t worry). I see a social game with the goal to buy “below the bid”. The ability to buy in a dark market and sell in an efficient lit one requires specialization in something (probably marketing). And if you get that right, you have an edge. And that edge accumulates more advantage until you are free to tell any fancy story that sounds better than whatever their actual specialty is.

I’m not saying be one-dimensional. But becoming very pointy in a single area is a better beachead from which to launch the various campaigns in your life. Those may eventually lead you far away from where you started which is almost certainly a sign of victory.

The world actually belongs to the obsessed. Talk to parents. They know. The whole extracurriculars pu-pu platter is a fallback plan to Operation: Optionality because their kid has not found their obsession.

[Related thought: Being hot, super-charismatic, or any number of things we would think of more as a talent are all forms of speciality that can confound how we see the success of a “generalist”. But even then, there’s no ceiling for someone who applies their natural gifts to a craft that benefits directly from them. This is the dream. Talent and interest synchronously rowing in the same direction.]

2) Should you care about market plumbing?

I’ve seen this sentiment several times over the last couple years:

The Seawolf guys (they were portrayed in The Big Short as the disagreeable investors in the weeds of bank accounting) have said something similar after a short tenure as pod PMs at Citadel. They said it’s important to understand how the pods move capital, even if they don’t think whatever they are doing is really investing. It’s more like trading with a focus on the coming quarter instead of intraday scalping.

If the pods are the marginal price setters, then understanding their behavior is important for traders or any investor whose investors judge them on the basis of months, not years. Nobody wants to be judged on the months of course, but not everyone can pick the investors best aligned with their horizon.

Speaking of horizons, if you care about short-run market behavior (days and weeks) but don’t have a dashboard tuned to flows, then day-to-day activity will remain inscrutable. If you care about intraday, then you are either in the same pool as HFTs OR you are staring for hours at illiquid order books to divine the story. Where can you compete?

Finally, these voodoo market movements can create opportunities for investors willing to underwrite a long-term thesis. This is admittedly tricky. Long-term investing is weirdly a difficult place for professional investors (it kinda feels like it’s a place that individual investors should have a better chance to prevail since they don’t answer to LPs, don’t need to benchmark, or worry about looking stupid).

Besides fickle LPs, professional long-term investors face feedback loops that can last a career, making them a) difficult to learn from and b) fertile landscapes for confirmation bias. Those types of edges are never provable. And when they exist, the horizon means less throughput…you aren’t getting thousands of at-bats to put the edge to work.

Insofar as a professional investor is able to convince investors to stay the course, this ability need not have anything to do with investing skill. In fact, a patient investor base paying an AUM fee is an arrangement that might make all but the most competitive investors a tad lazy.

The lack of feedback, throughput, and competitive pressures rooted in predictive performance metrics is a set of conditions that would not predict the best investors are looking to underwrite the long-run. This is a place to potentially compete. Of course, every silver lining has a cloud. Those near-term dislocations driven by the glorified day-traders might offer a better entry but the longer your holding period, the less your entry price matters. If you find a compounder for 15 years, it won’t matter much if you bought it for $80 instead of $100 because a bunch of pods got tapped to shed a factor.