“betting as a tax on bullshit”

🎙️Wrong numbers and why they survive Complex System Podcast

Patrick McKenzie interviews famous Wall Street quant and author Aaron Brown(Poker Face of Wall StreetRed-Blooded Risk) about his new book Wrong Number, which tackles a stubborn, nagging mule of a question:

“Why do institutions that produce bad statistics face so few consequences?”

I really enjoyed the interview and if Aaron’s other writing is any indication, the book will be outstanding. But I just want to excerpt a section from below that I appreciated.

Timestamps

(01:12) The agricultural demand curve discrepancy
(04:06) Why experts prioritize teaching over learning
(05:17) Institutional indifference to error
(06:26) The brand halo of high-status institutions
(08:34) Lessons from COVID-era decision-making
(10:19) Financial statements versus scientific rigor
(18:19) The difficulty of auditing and replicating research
(22:12) The CDC eviction moratorium and its justification
(23:34) The NTSB curbside carrier safety study
(26:41) Conspiracy versus incompetence in data manipulation
(30:05) Error correction in financial markets
(32:52) The culture of the advantage gambler versus the academic
(35:28) Betting as a tax on bullshit
(38:44) Using market pricing to evaluate risks
(41:04) The track record of scary predictions
(43:34) Environmental success stories and technological optimism
(48:21) Energy efficiency and the path to global wealth

Betting as a tax on bullshit (emphasis mine)

Patrick: I think Nate Silver calls this the “River” versus the “Village.”

Aaron, agreeing: As somebody said about Nate Silver, betting is a tax on bullshit. [Patrick notes: I associate that line with Marginal Revolution. The post coining it was, fittingly, about Nate Silver.]

Patrick continuingIn some fields, it seems viscerally distasteful that someone could be keeping a record of someone being wrong. That person is a threat to social harmony. When folks from the advantage gambler camp say, “You’ve expressed 99% credence that X is true; would you bet $50,000 at even odds?” it functions as a tax on bullshit. Some people find it extremely negative to be seen publicly responding to that in a repeated fashion.

Aaron: My friend Philip Tetlock did a book, Expert Political Judgment, which showed that experts in a field have less than random—or worse than random—predictions. The more prominent the expert, the worse the performance.

Here’s a good trader question. When somebody says, “Gold is overpriced, it’s going to fall to a thousand dollars,” you ask them: “How much would the price of gold have to go up before you admitted you were wrong?” For most people, it’s a blank look. They haven’t thought about it. A trader will tell you, “I think it’s going to a thousand, but my stop is six thousand. If it hits six, I’m getting out; I was wrong.” If you haven’t thought about that, you haven’t taken the first step toward forming a bet. If no evidence will convince you, then it’s an article of faith.

While humans use git to version defenseless letters and numbers into knowledge with traceable lineages, they themselves resist self-audit. To torture the analogy, betting is like a merge you can’t roll back for free.

I really just love the way Patrick put this:

In some fields, it seems viscerally distasteful that someone could be keeping a record of someone being wrong. That person is a threat to social harmony. When folks from the advantage gambler camp say, “You’ve expressed 99% credence that X is true; would you bet $50,000 at even odds?” it functions as a tax on bullshit. Some people find it extremely negative to be seen publicly responding to that in a repeated fashion.

These talkers want an infinite Sharpe. Return for zero risk. The bettor/trader/investor finds THAT “viscerally distasteful”. How dare you lay claim to the Holy Grail without so much as a dent in your armor?

It’s quite predictable that I’d enjoy such a podcast. I’m partial to idea of “taxing” lies and laziness, but the episode is also a welcome reminder that metrics are tabulated, presented, and interpreted by humans. There’s an irreducible amount of subjective cradling the objective.

Brown is the most recent messenger in a parade of writers I’ve been sharing here. Zvi Mowshowitz, Ben Recht, C .Thi Nguyen, Dan Davies, James C. Scott. Each one is touching a different part of the corruption-of-metrics elephant, whether it’s malice or incompetence or coordination failure.

Scott’s critique of modernism and its high-minded faith in optimization bridges the hubris of retro-futuristism to these voices warning us today. But the interview with Brown was alarming not because the examples he presents were defined, not by hubris, but by feckless apathy.

Retro-futurism was at least optimistic. But today’s failures are like forfeits because nobody felt like waking up for the morning game. Meh, there’ll be another one next week, and nobody will care who wins that one either.

“Hey, we’re going to Mars!”

“What’s the difference if I have to go with you?”

Despite our ascendant progress in science and mechanics, the human psyche starts at zero with every birth. An interminable game of Trouble with the pop-o-matic® bubble bonking every generation back to the home base.

The tension you feel “in the room” is that we have come so far and yet remain in the same place. The battle for hearts and minds on both sides of the argument will be fought with McNamara-esque precision. Countable, listable, sortable.

You’ll be a little more awake for it if you consider what Brown saw when he stopped to get a better look.

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

on the corruption of school grades

A few quick hits on the topics of education and learning.

Childhood and Education #18: Do The Math | 15 min read

So this happened at UCSD:

In the fall of 2020, 32 students took Math 2. In the fall of 2025, fully 1,000 students had math placement scores so low they would need it.

Oh. Well, then. That’s 12% of students at UCSD. Who all failed math, then?

Reviewing test results like these, you would expect transcripts full of Cs, Ds, or even failing grades. But alarmingly, these students’ transcripts did not even reflect profound struggles in math. Mostly, they were students whose transcripts said they had taken advanced math courses and performed well.

“Of those who demonstrated math skills not meeting middle school levels,” the report found, 42% reported completing calculus or precalculus.

… The students were broadly receiving good grades, too: More than a quarter of the students needing remedial math had a 4.0 grade point average in math. The average was 3.7.

Year after year, they fall farther behind, and it becomes more and more impossible for any teacher to admit that the students cannot do math and grade accordingly — since that would ruin the kids’ GPAs and college prospects. In this manner, they may make it all the way to college before they find out that they can only do math at a middle-school or sometimes an elementary-school level.

Oh. Well, then. The whole math educational system is a fraud. Once the SAT and ACT were eliminated as requirements for the UC system in 2020, there was no, as Kelsey puts it, ‘reality check’ on any of it, and that was that.

One observer said:

These kids were not doing anything wrong. They were lied to. They were told that they were prepared for classes they were not prepared for. They were told that they were excelling in classes that they were not excelling in. They deserved better.

Zvi isn’t going to let students’ convenient pleas of ignorance go unaccountable. And he’s right. The whole problem, and this sure feels like it goes on beyond math these days, is there is no accountability. It’s almost like the “too big to fail” virus spawned in 2008 infects every giant mass of human coordination effort with a “oh well” shrug of learned helplessness resignation. Home insurance doesn’t work in CA? Oh well. Guess you’ll just have to be rich enough to self-insure or sweat it out. Don’t have the attention span to read a book because short-form video fried the GFI in your brain? Oh well, guess you need parents who have enough discipline and bandwidth to fight you hard enough so you don’t log 12 screen time hours on a Saturday. Can’t do long division? Oh well, what do you need that for when robots are the future.

[I ended up titling this post “oh well” which compelled me to look up the Fleetwood Mac blues rock tune of the same name that’s often covered by guitarists. I forgot it had a distinct call and response structure and apparently I subconsciously had that bleed into how I wrote that section. Oh well I guess.]

Zvi:

I would love to not also blame the kids in all this, but that’s kind of nuts? If you can’t do the most basic math questions, and there’s an AP test at the end that almost no one in class even bothers taking, and you’re somehow opting out of every objective standardized test for math, how can you possibly actually think you’re passing Calculus for real?

Justin Skycak:

This isn’t just a UCSD problem. It’s even playing out at Harvard. Yeah, Harvard. The most prestigious university in the USA and maybe even the world. Last year they had to add remedial support to their entry-level calculus courses.

It should not be so difficult to select a Harvard class that is ready for Calculus. If the school that is the first choice of half of students can’t do it, then that is their choice.

Zvi’s post is about education, not to be confused with, umm, learning.

While the lower 99% get hollowed by accepting the unaccountable default programming, there’s never been more opportunities to avail yourself the ability to learn.

I’d rather share stuff in that vein rather than rolling the same complaints uphill.

Here’s Scott Young, author of Ultralearning, and one of my favorite resources on the topic of learning broadly:

Why I’m Skeptical About Efforts to Revolutionize Schooling | 9 min read

Whenever we have high-quality evidence that rigorously compares two teaching methods, the research invariably favors strong, direct instruction plus practice. Or, in other words, the exact stereotype of schooling that so many of the people asking me about school reform despise.

A “better” school probably looks more like the stereotype of an old-fashioned schoolhouse with kids sitting at desks, drilling facts and concepts that are patiently explained by a teacher. To the extent that school becomes more like free play, project-building or acting like a scientist, it will probably be worse.

Quantity has a quality all its own, and with enough well-integrated knowledge the result is expertise that seems almost magical to those who don’t possess it.

It all rhymes with Justin’s treatise on learning which I condensed and re-factored into:

🎓Principles of Learning Fast

And finally for today, this is a good lesson by PhD Benjamin Keep who researches and writes about learning. He explains a powerful study shwing the value of breaking a complex skill into sub-skills, focusing on them deliberately and in serial, only to watch your general ability improve at the complex super-skill. Learning is a lot of wax-on, wax-off. It was quaint to Ralph Macchio’s ears. Now we have all but forgotten.

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.