why selling an option because the “stock will never get there” is amateur vol thinking

In stepping through an oil put trade, I wrote:

As a junior trader I remember selling calls because “it’ll never get there”. I promise you there are many people who think like that. They don’t understand vol trading.”

A reader asked:

What’s wrong with selling OOM call options if vol is too rich? If it’s priced as a 1/100 event and it’s closer to 1/1000…that’s a good sell.

Here’s my response:

Given your assumption then I’d agree. But can you think of a scenario even with your assumption where it can still be wrong?

See this post How Much Extra Return Should You Demand For Illiquidity?

It looks superficially unrelated but at its heart is deeply related to the question. It’s like adding another dimension (axis) to your reasoning. The effect of path and many permutations of cross contamination is hard to model but you’d be falling for a streetlight effect to think it doesn’t matter.

Here’s a phrase to inhale:

“options on options”

What is the option to sell another option at some point in its life worth? Where do those “option on options” exist, and how are their value distributed across cross-asset states of the world?

I understand that’s a bit abstract but I’d maintain it’s the best avenue of reflection. But I can also address the question more concretely, even if I don’t think it’s the best answer to the question.

The concrete response is:

If someone is paying as if something is 1/100 when you think its 1/1000 why do you think you’re right? How can you parse the difference between 1/100 and 1/1000 in a non-physical system? Did the odds of GME going to $50 change when someone started betting that it would?

[2 years ago I wrote about CVNA in A Socratic Dissection Of An Option Trade. The stock is up 50x in 18 months.]

There is a good reason why one of the first things option market makers learn is the only way to price a far OTM option is via another option, ideally of similar moneyness. Because as soon as someone says “I bet I can drink 20 beers in an hour” your belief about how likely that is requires a massive update.

[In nerd language — the Bayesian prior on what a tail option is worth, based on some underpowered frequentist sample, is so low confidence that any real bid renders it stale and worthless.]

Something I’ve always found amusing — market-maker firms will interview kids out of college and pose a proposition like “I’ll give you 2-1 odds that I will get more than 5 heads in 10 flips” and the kids will say they’ll take the bet. The interviewer will up it to 3-1 and instead getting suspicious, some of the kids get even more excited. This is the most un-street-smart instinct imaginable. (I’ve heard that SIG has or used to have an employee who could reliably flip heads better than chance who was born to give these interviews. Maybe a reader can verify this.)

In the physical world, buying homeowners insurance doesn’t make a fire more likely. Well, stock and option prices are not the world of physics and chemistry. If someone says something is 100-1 when you insist it’s 1000-1 then I think you just enrolled in a epistemology bug bounty exercise.

(The wickedness of trading is that you’re unlikely to ever get enough trials to find out if you are right or wrong, but since the odds are 100-1 even when you’re wrong you’ll just go about your life as if you were right when in fact you learned nothing.

The corollary is you should be restrained in what you think track records can tell you if a strategy doesn’t do a huge sample of trades. A truth so inconvenient the entire asset management industry, GPs and allocators alike, ignore it.)

translating to “option surface” language

This is a useful practice:

Translate your sentiment into “option surface” language

For example, a reasonable posture right now is to be bullish…it’s also an uneasy one because it feels consensus.

Of course, consensus can be and often is right. It just won’t have a great risk/reward if it’s indeed consensus.

But that’s a bit fuzzy.

Instead, let’s reframe:

  1. A rally is expected therefore as it happens it’s “stabilizing”. Doesn’t catch anyone off guard, frog slowly boils. Vol dampening.
  2. A small pullback in the interim also not too crazy given how much we’ve rallied (broad indices up 1.5 standard devs in past 3 months)

In sum, the coin feels biased upward but left tail holds extra surprise (highly “destabilizing”) because its even more unexpected.

Translating this bullish distribution and vibe into options…

You’d want to own something like an ATM/OTM call spread and a tail put as an alternative to owning outright deltas.

[You could do enough of these option structures to maintain a long 100% position if you want.]

The question the advantage gambler would ask:

“Is the option market offering an attractive price for this posture OR is the structure more expensive than usual?”

You can get an approximate idea from looking at things like scatterplots of normalized skew vs vol.

[There’s a bit of push and pull. If the price for such a structure is historically cheap then you’d also be inclined to revise your impression of how consensus this posture actually is. By triangulating it with other measures of risk appetite (say credit spreads, bond yields) you can try to divine what the contradictions mean. For example, on Thursday, stocks and bond yields were up but gold, homebuilders, and REITs were down. That feels like a bullish economy outlook where bond yields are yelling “growth” while the reality of higher yields is weighing on both gold and real estate. But the fact that gold is weak says it’s not a reckless inflation story. BTC went up but that the deregulation energy muddies the water. Caveat: I wouldn’t conclude anything from 1 day’s price action. This is really just a demonstration of how you can look for contradictions to infer what the crowd is focused on.]

As I’m thinking about it, it makes me want to construct some canned structures that map to narrative postures like the one I described above. You can imagine a dashboard of such postures and the price for them over time.

Long call spread, and long OTM tail puts” is my option translation of the natural language sentiment.

[See the unlocked post a deeper understanding of vertical spreads to review why a long call spread which is a bullish position is also “long skew” — when call spreads are expensive think to yourself “market thinks we’re probably going higher but this is counterbalanced by a further left magnitude in the event it goes lower”]

All this said, I haven’t “looked up the price” which means wrangling data to see what the option market says about the full package but with SPY skews are all at middle of the road percentiles it’s probably average which means somewhat attractive if you think the distribution is more tilted than average.

moontower.ai: 90d SPY skews time series confirming average levels

On the role of options and investing

The nice thing about option expressions is the flexibility. The ability to customize the structure to fit your thesis. You can adjust the strikes to taste based on what you feel the distribution might be. You can select tradeoffs (perhaps you sell less OTM calls because you think “blow off top” is an underpriced scenario so you are willing to pay more up front premium). If you find the structure is cheap, expensive, or fair you can also decompose the legs to see what is driving the overall price.

To throw a bucket of ice water on people who want to have it both ways:

If you’re a passive investor and you sweat the shape and moves along the way, you’re not really cut out for what buy and hold requires (it’s a compensation for patience not labor).

The solution is most cases is simple — size down until you are comfortable not looking. You can expect a 25% drawdown once a decade at least.

If you spend more time thinking about the nearer term shape of returns…then options are more surgical. The outright stock price is a blunt compression of an idiosyncratic distribution into a flat 2-D number. Options are the 3-D version. Most people shouldn’t care about the 3-D but if you do options are the weapon of choice.

By getting better at options thinking and “having a vol lens” you can parse what the surface says and compare that to what you think. The tighter your thinking the easier it is to map it to the options surface. Since it’s professional’s job to think tightly I they have more to gain from adopting a vol lens. (If you want to make a stronger statement you could say that not understanding the best way to express their views is at best an invitation to be outcompeted, at worst negligent.)

For the retail investor, fuzzy “I’m just along for the passive ride, I’ve outsourced my pricing to the market, and just have to decide my size” is fine. But if you want to take more control, options offer granularity which steer you to sharper thinking.

adverse selection in the option job market

Friends,

Today I’m going to both be a student and speaker at Ricki Heicklen’s Quantitative Bootcamp in Berkeley. Ricki is a Jane Street alum who got on my radar when I heard her interview with Patrick Mackenzie.

I summarized the convo in A Jane Street Alum Teaches Trading but it’s still a long article. The interview is dense with insight. Very rare for this stuff to be presented in such an accessible way in public.

Early in the interview Patrick asks Ricki to complete this sentence:

“I’m going to impart a bit of information upon you to get you ready for understanding the US equities markets…” – if you only had one sentence, what is that?

Ricki, without hesitation:

The number one sentence for purposes of trading, in general, is to think about adverse selection.

The questionnaire she give to incoming students is loaded with tricky examples of adverse selection hiding in seemingly innocuous scenarios. You can get some flavor of this in her post Toward a Broader Conception of Adverse Selection.


💡Aside: Polling has been a popular topic recently for obvious reasons. Adverse selection is a sibling of sampling bias. It’s the mother of monkeywrenches in statistics. This back and forth between Ben Orlin and Jim O’Shaughnessy has several fun, yet profound, examples of sampling bias.

Mathematician Ben Orlin on Infinite Loops podcast audio & transcript (6 min)


Fellow Jane Street alum, Agustin Lebron, has also emphasized the significance of adverse selection. In his exceptional book, Law of Trading (my notes), chapter 1 is about motivation. Chapter 2 is, you guessed it, Adverse Selection.

[The obsession here is not misplaced. SIG or any other market maker is going to dwell on this because markets are not kindergarten — your counterparty wants to make money by disagreeing with you so understanding if they are safe to trade against is the a primary objective.]

The chapter includes several great examples of adverse selection in financial markets, but as every chapter does, it closes with practical applications that are pertinent to anyone not just traders. I’ll use this extended excerpt about adverse selection in the labor market to setup today’s discussion (emphasis mine):

Adverse selection in the job market appears on the side of both the employer and the prospective employee. Employees are looking for the most attractive job they can find, while employers are looking for the best candidate for the job.

Prospective employees are subject to various selection pressuresnot all of them adverse:

  • Given that the company is looking to hire employees, things can’t be going all that badly for the firm. This could have a positive selection effect, for once. Nevertheless, maybe the company is hiring because people are leaving and they’re having trouble finding hires. It’s a double-edged sword.
  • The job description is likely to be embellished, at least a little bit, especially for less-attractive jobs.
  • The interviewers in a company are typically better-than-average employees since they’re the ones the company chooses to represent them to potential hires. Thus, the applicant sees a rosy picture of the quality of her future co-workers.
  • Employees typically only seek out new jobs every few years or so. As a result, their skill at job finding is lower than the companies’ skill at candidate finding. This asymmetry of skill and knowledge works in the companies’ favor.

Employers, however, suffer significantly greater adverse selection, since in the end the employee is the one making the final decision of either accepting or rejecting a job offer [Kris: the candidate holds the last option — it’s like the asymmetry in backgammon with the doubling cube — you must have significant edge to offer it, but you only need to have a 25% chance of winning to accept it. Btw, this was an interview question I had back in 1999]

  • When hiring people with prior experience, the applicant pool skews in the direction of lower-quality workers. This is because good workers will be preferentially incentivized to remain with their current employers. On average, therefore, people with prior experience looking for jobs aren’t as good as those who have jobs (Greenwald, 1986).
  • The process of interviewing to decide whom to hire is an imperfect one. Companies will therefore not be able to sufficiently distinguish between good and bad workers, meaning they will tend to squeeze offered wages toward the average. This is advantageous for less competent workers, who, for the most part, will be the ones looking for work, and disadvantageous for good workers, who will be driven away from the job market by the lower-than-deserved wages on offer. [Kris: this is the so-called “lemon problem” in the used car market]
  • Potential employees will select the best offer from all the ones available to them. Good workers will have a large pool of available offers and will pick the best one. If a given employer isn’t universally known as the most desirable one, then it’s fair to say that a worker who accepts an employer’s job offer does so because she couldn’t get a better one elsewhere.

A reasonable blanket assumption is the employer faces a larger adverse selection problem than the candidate.

But what I want to talk about is how with experienced option traders I have seen this flipped. Well, maybe not flipped, that’s hard to say but I can pinpoint a somewhat narrow but substantial area of adverse selection that I’d expect was more prominent in the past 5 years.

Whenever I have a call with a trader evaluating an opportunity I warn them about this because I’ve seen it time and time again.

No math or charts today. This is a topic for experienced professional option traders although I’d bet it could be generalized faithfully to anyone with valuable experience who is being sought after. You can make the adjustments for your own field.


I’m going to be very direct since you are not a learner or novice. If you’re at this point you understand the angles. You are already damn good at what you do. The failure mode here has nothing to do with your competence as an option trader or risk taker.

The failure is one of expectations.

I’ll lead with a blunt warning:

Beware asset managers trying to “get into options”

The entire options ecosystem has exploded in the past 2 decades. Pick your buzzphrase:

“VIX complex”

“Tail hedging”

“Iron condor”

“Covered Calls” (I’m old enough to remember these being called buy-writes)

“Dispersion”

“Hedged equity”

“zero DTE”

Even the word “optionality” metastasizing from finance to VC (that verb was pointedly chosen but also to be fair stock-based comp and option grants are good reasons for tech workers to get nerdsniped by option lingo).

Netflix has a film about a human named RoaringKitty trading options on a brokerage called Robinhood.

The growing awareness of options is self-evident. (I like to think moontower has a sprinkle of guilt in the matter.)

Since asset management is as much about sales as it is about alpha, you can see how the democratization of option knowledge has served as a fortuitous “commoditize the complement” strategy for opportunists who think in terms of “product” not edge.

Simultaneously, (and I’m going to paint with wide brush), a class of crypto moguls blessed with more nerve than trading acumen, have coffers from which they can punt on new businesses.

If you are a successful option trader looking to build a business or graduate to a more senior situation, this backdrop is a godsend. You have experience that is:

a) highly complementary or non-overlapping to the people who covet it

b) the demand is coming from businesses that are sitting on lots of capital given where markets are broadly

In other words, there’s a lot of money out there that wants YOU. And since anyone whose ever fantasized about flipping the desk in their bonus meeting after getting a 5 out of 5 on their performance review but the cash is your “median expected bonus” knows — haggling over pay with other option traders is Gold medal round of the gaslight Olympics. And I say this during an election week.

The contrast of being woo’d by rich business people who don’t really understand YOUR business is a welcome (and foreign) asymmetry.

Unfortunately this attractive setup is also the danger.

I’ll pose this question and I hope I get some responses…do you know of any firm that did not deeply understand options that successfully got into vol trading by hiring an option trader to build the business?

I’ve seen option traders launch funds from scratch. I’ve seen option traders join pods or move from one trading firm to another. Banks have revolving doors for traders.

But when I think of instances where an established asset manager tried to “get into options”, none have lasted.

my theory

Non-option managers do not understand (nor desire) the true shape of a vol trading p/l.

Here’s a few flavors of disappointment:

  • They expect steady profits only to discover that only the market-makers operating at scale make money every day. That’s not a reasonable expectation.
  • They expect to make money when the market gets stressed only to discover that dispersion gets hammered on the first leg down. Of course, experienced option firms know this and even embrace the pain on the token short corr position because the real opportunity is coming and your going to make the real money when the environment relaxes. Of course, that p/l stream will look correlated with the asset manager’s core business so that’s disappointing.
  • Build an option business with a long vol/gamma/tail bias. Lose patience or faith in what that anti-correlated stream does to your business holistically. Focus on the line-item drag that this new business is. Nudge the option trader you hired to increase the batting average and get disappointed when you find out that swinging for contact means sacrificing power.

red flags

If you are being recruited to build an option business for a firm that is not native to options, here are some red flags:

  • Not understanding the shape of dispersion p/l
  • Wants to impose risk rules that do not make sense in options. Stop-losses do not make sense in options. You want to constrain your risk a priori so that it’s survivable (however defined) not have a risk rule that has memory since the best opportunities in vol (a domain that has mean reversion) are seeded by pain.
  • Doesn’t realize how expensive/laborious it is to build proper risk monitoring infrastructure, security master, and back office ops. If you are building a significant option business from scratch and they expect p/l in year one, they are either delusional or willing to throw a ton of money at the build-out to make it go faster. The comp deal they offer you should be a big clue (I say this not just from personal experience but by helping other senior traders weight their offers — I’ve helped at least 5 people with this in the past year alone. There is a wide canyon between a serious firm’s deal and a “I heard there’s money in options” firm.)

considerations on more promising sources of expansion

While I’m generally bearish on the prospect of a happy marriage between asset-management suitors and option traders, I’m more optimistic on non-option prop firms expanding into options.

For example, HFT firms are in capacity-constrained businesses. But they are cash-rich, smart and have economies of scale and synergies with other public market strategies. They are more natural fits for high volume option traders.

Caution is still advised.

A few ideas for candidates to keep in mind:

  • HFT firms are not in the business of warehousing risk. They are flippers. Option trading is a lower Sharpe (should still be north of 1 and with attractive anti-correlation and perhaps even tail properties). What’s the suitor’s commitment to something that will expand their capacity but slide down the risk/reward continuum? Sitting next to an HFT’s equity curve is gonna make an option trader look flabby. Again, what are the expectations?
  • Single stock option traders pay attention. You know as well as anyone that the requirements and nature of trading single name vol are vastly different than index, commodity, fixed income, fx or other liquid markets. Especially in options. The barriers to entry in the liquid markets are lower so firms that survive their inception and move on to expansion will typically have started in index or futures markets. Which means they don’t know what they don’t know when it comes to single-name. Don’t presume their understanding just because they are smart and successful up until this point.

 

closing words

Candidates, you’re in a mixed position. You are already successful. But you are coming into another part of your career where it’s not just about trading but building. There might be lots of details of your business thus far that have been abstracted or handled for you. Things that are not market-related that you don’t enjoy thinking about.

Now you need to be the one with all the answers. You will need to delegate, project-manage, and communicate to stakeholders who might not speak your compressed dirty trading language.

You will also face what I call the “realtor problem”. An honest realtor is forced to compete with the hooker who shouts the highest price to secure the listing — “you have the most unique house on the block, I’ll get you 20% more than neighbor got”. There will be candidates that pump up the suitor’s expectations and minimize what’s required. It’s hard to compete with that, especially since they will sound far slicker than the sleazy realtor. This is the big-leagues.

Matching to a mutually rewarding relationship can take a long time. Anecdotally, between garden leaves and the innate specificity of roles, you can easily expect a full search to take up to 2 years and even once you are in process, 6 months to hammer out details is not abnormal.

It’s incredibly expensive to let hope overwhelm logic.

Cold feet is one thing, but don’t ignore nagging feelings. If it feels overly provisionary, opportunist, or like the suitor is trying to time something you should be on high alert. A quality connection exudes patience, long-termism, and ambition — you don’t move needles by thinking small. And you don’t hire people who can deliver on ambition by playing games with them.

I’ve definitely seen deals stand out as “how a serious employer treats a quality candidate”. Deals with experienced traders will often allow the candidate to tune their utility curve by trading off between guarantees, percent of profits, base and so on. This makes sense. Firms are in a better position to absorb the risk of the relationship than the individual so so they can allow some latitude for the candidate to choose across some indifference frontier. This costs the firm nothing, but increases their chances of landing the candidate.

[One word of caution: anytime you are negotiating your share of the profits you are implicitly negotiating the amount of risk you can take. Getting a high payout on a deal where the boss asks why you lost $10k today is probably not what you had in mind when you agreed to the job. Expectations here are everything. Be explicit. On a similar note, if you are on a high payout deal but it takes 6 months to get your accounts set-up is garden leave without the view. At the end of the day, bargaining position is everything. I wrote this post 5 years ago and don’t link to it enough — You Better Understand The Difference Between Contracts and Power]

If you are in a position to help grow a business, the most important decisions is not a strategy or trade — it’s the WHO. Do not grant the benefit of the doubt easily. There’s too much time at stake.

I’m harping on all this out because I have repeatedly found that the superficial similarity between options trading and other investing businesses is strong. But this masks the inevitable moment when the business owner sees a a bad run and realizes the contour of this new business is not what they bargained for.

At this point, everyone has wasted a lot of time and money.

The single biggest problem in communication is the illusion that it has taken place — George Bernard Shaw

 


A short take on my own experience

I was fortunate in my career to work for people that were consummately patient and respectful. In other words, they didn’t make the inevitable bad runs worse. They understood the shape of option trading. They understood what it means to “not result”. They offered perspectives but ultimately it was up to me on how to maneuver. I was allowed the space to work out of my slumps on my own. Patience is never endless but I never even saw the hint of where it was starting to deplete. (If anything, and I’ve talked about this before, my struggle was in being less cautious. They trusted my instincts more than I did.)

 

Final Postscript

Here’s an excerpt that you can choose to weigh in your assessment of a suitor’s incentives, obligations, pressures and how they’ll be as bosses.

It’s SIG director Todd Simkin explaining the value of being a private investment company without outside investors on the Capital Allocators podcast (link):

We’ve been in a really nice position of having the most patient capital of all. One of the problems with hedge funds is that they have to frequently manage to not just quarterly reports but monthly reports or even weekly and daily reports. So they’ve got to show that they’re staying with the strategy they have outlined for their investors and that they’re showing regular returns.

Our investors are the principals of the firm. They understand the risk. When we take outsized risks, they understand what they are. They’re the ones who are driving it. If I want to put on a $100 million insurance risk where the full exposure is to the winner of the Super Bowl. I’m not worried that if we lose on that risk that I’ve got to now explain to a whole bunch of people why we just lost their money. Instead, I’m calling one person and saying, hey, are you okay with me taking this risk? Here’s the edge I think I have. Here’s the rate at which I can sell it. And he says, yeah, that sounds good. And he’s monitoring it and he’s asking about it and he’s checking on the health of the quarterback through the season, all the things that you think would happen when you have that type of risk on.

But because we’ve been able to be patient, we’ve been able to stay in businesses and grow businesses that have had downturns. And at the same time, we’ve been able to shut down exposures where other people would say, sorry, we have to have our long short equity exposure because that’s what we do. That’s the business we’re in. That’s what we’ve told our clients we’re going to be doing for them. So even though that’s not the strategy that’s optimal right now, we still have to allocate whatever percentage of our portfolio to that. We get to shift dynamically. We get all of the benefits of having a large capital base with all of the benefits of having a small number of decision makers at the top who are weighing in. They’re not putting artificial rules in place that we might have seen if we had ever taken outside money.

 

Stay groovy

☮️

the option market’s point spread

This is Part I of a discussion of VRP

The volatility risk premium (VRP) is the notion that options are generally overpriced. Not all the time, not in every name, not across the entire surface. Just in general.

What to do with this information is another matter.

If their premiums are higher than their cost to replicate you can sell them, hedge, and earn a profit. If the expected value of owning an option is negative you can still buy them to make an existing portfolio safer. The combination can be a better proposition than looking at any of the line items in isolation.

Either way, we want to separate price from value.

In Primer #8: Top of the Funnel: Cross-Sectional Fair Value, I define how moontower.ai computes VRP but we’ll use a slightly simpler computation for this post:

VRP = 1-month implied vol (IV) / 1-month realized volatility

  • The implied volatility is “constant maturity”. This means we interpolate between the 2 closest expiries which surround 30 calendar days into the future. The interpolation is linear in log(time). Or you can linearly interpolate variance (ie volatility squared) and convert back to volatility. Same thing.
  • The 1-month realized vol for this post is simply the sample standard deviation of the last 20 daily logreturns annualized by √251

If implied volatility is 20% and the realized volatility is 15% then the VRP is 20% / 15% or 1.33.

In the moontower tools we’d refer to this as 33% or VRP – 1 to represent it as premium/discount.

If the implied vol was only 14% then the VRP is 14%/15% – 1 = -6.7%


Forward-looking vs backward looking

Implied volatility is set by market consensus. It’s the number that makes an option model spit out the price for calls and puts that actually trade. It’s both forward and backward looking.

It’s backward-looking because traders use history to handicap what volatility can be. SPY and TSLA behave differently. You’d love to buy TSLA options for SPY implieds and sell SPY options at TSLA implieds. In fact you’d pay for the privilege. So would everyone else. Your bid price to this is a pairwise microcosm of how the options surfaces in the world arrange themselves in a giant, relative matrix. Much of that matrix is pulling from how these assets move and co-move. That’s historical info.

Right now, is a great example of how option markets are also forward-looking. With the US elections approaching, there is an outsize chunk of 1-day variance waving to us from nearly every option term structure. This is TLT with the maturity dominated by the election highlighted:

 moontower.ai

This volatility is less driven by the past moves. a projection of past moves is blended with an estimate of how much bonds might move on election day.

💡See Understanding Implied Forwards to learn more about the blending.

This highlights the tension of VRP ratios. The numerator knows things the denominator doesn’t.

From the Primer:

The VRP ratio divides IV, a forward-looking measure, by a lagging realized volatility. We understand both the embedded utility of such a measure —vol clusters, so recent volatility is correlated to the expected future volatility; and the tension that the numerator anticipates the future while the denominator reports the past. But there is a wrinkle around known events that distort our interpretation of the measure. The following examples characterize the distortion:

1) Upcoming earnings or FOMC day

Implied volatility will anticipate the extra variance associated with the upcoming event, artificially widening the VRP. Professional option traders will use quantitative methods to extract how much extra variance the market is assigning to the event to “clean” the IV. Ideally, VRPs would be adjusted for known events. There is no single accepted technique for cleaning the IV but the quick solution is a judgment — “XYZ has an abnormally high VRP, but I just noticed it has earnings next Tuesday”. [The moontower.ai roadmap includes providing a calculator to allow a user to extract an event. In the meantime, you can use term structure tools (described later) to “see” where the market anticipates events]

2) Earnings have recently been reported

This is the opposite failure mode of the VRP measure. A stock had a large earnings move which carries significant weight in the realized volatility (the denominator of VRP) but the IV is looking forward to a period where there is no news expected since the company has already given guidance, had a conference call, and reported financials. This will artificially depress the VRP. Again, judgment is in order. It’s best to compare the IV to periods of realized vol without the earnings move.

Quants have spent many a brain cell trying to forecast volatility. For good reason. If your forecast is better than the one embedded in the implied, you could Doordash Sizzler like a boss.

In the moontower.ai tools we can see how well the implieds predict the realized vol.

This is double-paned chart is XBI 30d IV vs 30d realized vol. The top panel shows how the implied vol is usually a bit rich to the realized but not always.

In the bottom panel, we toggle “Lag IV”.

This lags the implied vol so we can see how IV tracked the ensuing realized vol. You are looking at the realized vol next to what the implied vol was a month ago (hence the “lag”).

moontower.ai

The red box on the chart is August 5th. The realized vol naturally shot well over the IV from a month earlier (in other words, if you bought XBI options in in July they were cheap compared to the movement August 5th had in store). In addition, the top panel shows how IV itself also shot up on August 5th. But as you look back at the bottom panel, you can see how that elevated vol turned out to be much higher than the realized vol that unfolded the remainder of August as the stress seemed to depart as quickly as it showed up.

For the rest of today we will examine data from the past year to get a feel for the VRP in lots of tickers. VRP is a popular topic in options, you’ll want to understand its shape.

It’s the option market’s point spread.

Setup

I looked at closing data for the past year (10/11/23 to 10/16/24) to fetch 30d IVs and 20d close-to-close realized vols for each trade date.

📅There are about 21 trading days in a 30d calendar month so the time windows are lined up well enough.

Table

The table shows the average VRP (as well as the standard deviation of the VRP) and the average lagged VRP which tells us the average premium/discount the implied vol had to the ensuing realized vol. To a sports bettor, this is like asking “how did the realized vol do against the spread?”

Observations:

  • SPY, on average had implied vols 9% premium to 1-month realized (ie if 1-month realized was 10% the implied was 10.9%)
  • There is a positive VRP in most names.
  • The single stock names at the bottom of the table were underpriced volatility on average. A glancing thought — vol traders have noted (lamented?) extremely low levels of implied and realized index correlations for the past couple years with index volatility trading historically low compared to single stocks. This high-level snapshot shows the single-stock vols are not even absolutely expensive.
  • Many of the foreign vols were much higher than the realized. HYG is always expensive but trades at an absolute low level of volatility. One thing to appreciate about volatility is that standard deviation is only one varietal of risk. In the presence of skew, focusing on standard deviation is misleading. The standard deviation of a balanced coin flip is 66% higher than a biased 90/10 coin flip. But would you conclude the balanced coin is riskier? See 🤡Skew Is A Hall of Mirrors
  • Finally, note how well the average lagged VRP affirms the average VRP. If you average across all these names for the past year both the VRP and the lagged VRP (ie how the IV did compared to the ensuing realized) stood at an 8% premium to prior and eventual realized vols! The names below the slope =1 line have on average outrealized their implied vol.

     

Crossing a 4-ft deep river

You know how this story goes. If you want to cross a river, it’s not enough to know how deep it is on average.

So far all we’ve done is look at averages.

Looking at all the tickers zoomed out, the average VRP by name reflects how expensive the options are compared to the realized even on a going-forward basis. It’s a buzzkill.

Until we look under the hood.

Let’s open up SPY.

The x-axis is the VRP while the y-axis is the VRP that end up being realized over the next month. This is not well-behaved. There are times when the VRP is

  • The upper left quadrant = “low VRP but realized ended up underperforming”
  • The lower left quadrant = “low VRP and realized outperformed the low already discounted IV”
  • The upper right = “these were good sales — vol that screened high and realized couldn’t catch up”
  • Lower right = “vol was high and turned out not to be high enough”

We can zoom a bit further by halves.

When VRP is negative…and VERY negative:

When VRP is positive…and VERY positive:

And finally, the time series which shows how the serene surface behavior of averages is really a river of many depths:

  • We see that when the VRP dips, it’s often the case that the realized VRP (red line) spikes meaning that the low VRP wasn’t low enough! Selling low VRP can absolutely payoff. The reason I added the IV line in there is because, low VRPs are often coincident with high volatility. Why? Because the market expects mean reversion back to more normal levels of volatility. What surprised me about this chart is how low VRPs even at low IVs failed to reward the option longs.
  • You can again see Aug 5th — when the red line or realized VRP goes sharply negative it shows how the realized vol was much higher than anything July anticipated. You can also see the VRP (blue line) collapse shortly after the stress as the options market discounted the previous elevated RV and looked ahead to more normal times.
  • A general caution — you cannot tell from this char whether the high or low VRPs are being driven by the numerator or denominator. (This is why the first 2 filters in the moontower.ai funnel are the Dashboard and Real tools explained in the Primer — a glance at both of those charts and you know what’s fueling the ratio.)

     

Let’s do one more. GLD.

I’ll narrate the numbered sections:

  1. IV is elevated but realized vol must be high since the VRP stayed muted. The options ended up being highly overpriced as the spiked red line indicated the realized VRP approached 60%! We can see that the IV cratered from about 16% to 11% from Oct to Nov 2023. Considering how the VRP (blue line) rose during that period we can infer that the realized utterly collapsed.
  2. When the vols got under 12% they were a huge bargain. The lagged VRP showed the vols being much cheaper than the ensuing realized.
  3. Once again, IV popped higher, VRP didn’t follow, in fact the options were trading at a large discount to RV — and correctly so it turns out. The lagged VRP was brutal for the longs.
  4. The lowest lagged VRP got all year corresponded to vols and VRP getting cheap. The obvious trade paid off.
  5. Another relatively obvious one pays off — IV and VRP spike and sure enough those vols couldn’t support the ensuing realized.
  6. This was yet another obvious one that paid — the one I wrote up in Flash post on GLD vol and Options Are ALWAYS About Vol. Vol roofed, VRP popped and the ensuing realized massively underperformed.

Closing thoughts and what’s next

Option markets are games not problem sets. You don’t solve them.

There’s no single killer metric. You are constantly triangulating against everyone else whose is also triangulating. You can’t look at VRP in isolation.

  • What’s driving the numerator vs denominator?
  • What’s the distribution of the variable in the numerator vs the denominator?
  • How do other tickers compare using the same sets of lenses?

While none of the math here is beyond 6th grade, this is a lot of mental shape rotation. It’s cognitively demanding every time you hear or read “VRP” or “lagged VRP” if you have to translate in your head “high VRP means IV is high compared to…blah blah”.

Just like learning requires looking away from the page and re-stating what you’ve studied in your own words, you need to practice. Look at option chains and vols, try to come up with trades and talk yourself out of them. What you can’t talk yourself out of becomes a candidate.

If you’re already reading this far you’re paying for the substack — sign up for moontower.ai, you get the substack for free, and you can practice every day with the tools. (I say it and I mean it — the cost of the software rounds to zero if you actually trade. The true cost is the practice of getting better.)

[Btw, if you are a professional whether a broker, trader, writer, investor this lens will tell you quite a bit about what the options market thinks about a name which is useful for taking risk or providing unique context to clients, readers or stakeholders who are trying to pull signal from noise.]

A word on data hacking

  • I used overlapping data since I’m looking at rolling 20-day windows every day over the past year. This “shrinks” the sample size tremendously. It’s ok for this context since we aren’t drawing conclusions or trying to estimate frequencies. The point of this post is to give you the shape of VRPs and to inspire your own explorations by giving you some angles you may not have considered.
  • In the time series chart, I’m narrating from left-to-right. But when I say the IV is high or low, presumably versus the “mean IV” green lines, I’m cheating. The mean IV is based on the 1 year history of IV that we studied but if it’s March 2024, my definition of “high” or “low” vol will depend on prior data only. The green line is “snooping” into the future if you read from left-to-right. One could correct for this by keeping track of what percentile or z-score the IV is in compared to its prior history (we use percentiles in multiple contexts in moontower.ai — they are suitable for identifying unusual values).

Next…

In next week’s follow-up we go bit deeper to appreciate how you can manipulate the inputs into VRPs to identify potential vol trades. I said VRP is the option market’s point spread.

Except for a tiny wrinkle.

There’s no single line.

stepping through an oil put option trade

Back on Oct 17th, I sold Z24 WTI (oil) 67 strike puts unhedged.

I explained my reasoning in this thread back when I did the trade. They were the equivalent to the USO Nov 15th 69 puts (I said Nov 22nd expiry but that was in error.)

I covered the WTI puts on Thursday morning. I published this thread when I covered them. Here’s a mildly edited version:

We’ll use the USO puts to write the post-mortem of a roughly 2 week trade. I hope its super educational.

Let’s start with the vibes.

Markets feel a bit, I don’t know, ahead of themselves. Everything but oil popping (til today). Rates & USD higher.

I’m less bullish on oil (and broadly bearish).

I cut oil length and bot t-bills this am.

Let’s get to the specifics of the “cutting length” trade because there’s many ways to do that. But my directional bias coincided with wanting to buy back my short vol (the moontower mantra — don’t touch the options without a vol lens).

Why?

Vol has sufficiently relaxed in oil since i sold the puts. The put skew was at normal levels when i first sold the 30d delta puts but the vol was high. Since spot/vol corr was positive that made them seem extra high!

  • Today there almost no skew in those (now) .29d puts
  • The implied vol is below realized (granted realized is on the high end of the range)
  • AND the election is getting negligible vol premium in oil

These pics show the negative VRP and negligible event premium assuming 35% fair base vol (which comes from eyeballing the USO vol term structure).

moontower.ai

While that explains the how and why of covering the position, let’s understand the p/l attribution of the position while I held it. We do this with the same type of charts I’ve been showing post-mortems with.

I’ll narrate where your eyes should go so it’s easier to learn.

If the puts were hedged the trade was steadily profitable except for 2 days out of 11 when the market popped.

See the yellow boxes on the red line:

Every day we can see the contribution to the hedged p/l from 2 components:

  1. realized vol p/l (tug of war between gamma & theta)
  2. vega p/l (change in IV)

The yellow boxes are examples of the daily decomposition.

Look what happened on Friday 10/25’s big down move…the hedged p/l was still positive. Yes, you got hammered on the realized p/l but vol got slammed! The put skew was in fact unjustified. The down move was what I call stabilizing to the market

Down moves aren’t normally stabilizing but my idea was that the Middle East conflict was driving the high vol so in this context a down move would be stabilizing so the total vol was unjustified if oil is lower.

(Ofc I was naked short the puts so that Friday was still a tough p/l day because i experienced a rough delta p/l but overall it was buffered by the puts underperforming)

Over the life of the trade, on a delta hedged basis you would earn $.45 being short the option from $1.76 On an unhedged basis it was $.78 (I actually made more than that because I actually sold the options closer to $2 bc the stock was about the same place it is right now, $71.85)

More importantly let’s look at the cumulative p/l attribution:

Almost all of it came from vega. The option was well-priced from a realized vol point of view!


This all ties in to my general gestalt of “short where she lands, long where she ain’t” bit. If vol is going to relax when it “gets there” then you don’t wanna use the option to bet it’s gonna get there. And if everyone thinks it’s “not going there” then when it does it will destabilize and you’ll wish you owned that option.

As a junior trader I remember selling calls bc “it’ll never get there”. I promise you there are many people who think like that. They don’t understand vol trading.

[An aside: That statement sounds more incendiary than I’d like. It troubles me I can’t fully articulate it. It’s a bit of an ink blot test. It’s understandable if you find that unsatisfying but the raw reality is indifferent to both of our dissatisfaction. In truth, there was a point of separation somewhere along the evolution of trading careers where as things got more competitive from the floor days to today, the traders who were copycatting disappeared into other parts of the business. When trading morphed from time/place advantage edge to positional edge it exposed the copycats lack of deep options understanding. Before Hollywood, there was a “me too” era on option pits across the land, where you only had to be savvy enough to identify who was smart and just make sure you yelled “buy’em” at the same time.

There are a lot of people who sound like they get vol trading. In fact I can’t fully imagine how hard it is for someone who’s not super experienced to tell the difference. The problem with codifying a “trading Turing test” is the same one interviewers have with candidates — as professional-grade info gets disseminated it’s hard to know if someone has earned it or parroted it.]

One of the savviest oil options traders I ever knew had a good formulation:

He’d buy those nominally cheap (but vol expensive) weeny puts when he was bullish. Because if the market dropped he just wanted to own what I call “the trap door” to protect what he really wanted to do…get balls long

In my own trading, i wanted to own the trap door. Whatever everyone thinks is impossible is the option i want. Stick’em in my back pocket and if it ever comes into play I’m the only one with 2 hands on the wheel

I admit this instinct was much stronger when i was trading a big book and i don’t have it as much now (that’s another discussion altogether).

Anyway, I hope this was overall educational. There’s an art to this game called options. If anything i maybe it gets the ole mind bicycle spinnin’ in such a way that even if you don’t trade options, it can mentally upgrade your whole investment decision OS.

“negatively priced lunch”

Markku Kurtti is an engineer in the telecom world. His outsider quant take on portfolio construction is beautifully derived and intuitive.

I strongly recommend his interview with Corey Hoffstein:

🎙️Diversification is a Negatively Priced Lunch (Flirting with Models podcast)

His blog is also outstanding. I’ll point you to this post in particular:

How much skill a concentrated stock picker needs to beat a diversified benchmark? (17 min read)

I summarize key findings below (with the aid of an LLM). The “Moontower highlights” are direct quotes from my kindle.

The central theme:

For a stock picker to successfully manage a concentrated portfolio, they must generate sufficient alpha to overcome the inherent risks and volatility associated with fewer holdings.

Supporting points:

1) The Balance Between Concentration and Diversification

Concentrated portfolios inherently carry more risk due to idiosyncratic variance, or the unique risks associated with individual stocks. To overcome this risk, stock pickers need to generate enough alpha to offset the “variance drag” — the reduction in expected growth rate caused by high volatility.

🟡Moontower highlight: “Portfolio construction of a skilled stock picker is a compromise between enhancing alpha by concentration and mitigating idiosyncratic variance drag by diversification.”

2) Importance of Consistent Skill and Alpha Requirements by Stock Size:

Different types of stocks require varying levels of alpha to beat the benchmark. Larger, more stable stocks typically require less alpha than smaller, more volatile stocks. Consistency in skill is crucial, as erratic performance increases the minimum alpha required to compensate for the higher risk.

🟡Moontower highlight: “Assuming perfectly consistent stock picking skill over time, 10-stock big stocks portfolio has historically required roughly 0.5 percentage point (pp) annualized alpha, small stocks ~1pp and micro-caps ~2pp. High E/P, E/B, Mom and B/P styles, in the universe of all stocks, have required roughly ~1pp and low E/P, E/B, Mom and B/P styles north of ~2pp. Low E/P style (smallish growth stocks with low profitability) have required the highest 2.55pp alpha.”

3) Risk of Concentration Without Skill

Concentration magnifies returns but also heightens risks. Without genuine stock-picking skill, a concentrated portfolio becomes increasingly likely to underperform over time. The document cautions against relying too heavily on concentration to boost returns without sufficient alpha.

🟡Moontower highlight: “But concentration is risky. If you concentrate and don’t have genuine stock picking skill, time will be your enemy.”

4) Circle of Competence and Style Diversification

The post emphasizes the value of investing within one’s “circle of competence” — areas where the investor has the most knowledge or advantage. However, it also warns that focusing exclusively on a single style exposes investors to style risk.

5) Predictability of Variance Drag Over Return

Idiosyncratic variance drag, the penalty for concentrating in fewer stocks, is more predictable than expected returns.

🟡Moontower highlight: “Idiosyncratic variance drag differences are easier to predict than expected return differences. It is therefore safer to increase diversification, which reliably decreases minimum alpha requirement, than to increase portfolio concentration to enhance uncertain alpha.”

🟡Moontower reference: The idea that volatility is more predictable than returns is a foundational principle in portfolio management. See Know Nothing Sizing

6) Lottery Preference in High Variance Styles

Some investors are attracted to high-idiosyncratic-variance stocks with potential for lottery-like returns leading to lower forward-looking returns.

🟡Moontower highlight: “Some investors may prefer stocks that may pay off big and this is exactly what idiosyncratic variance delivers: large dispersion of returns among individual stocks.”

🟡Moontower reference: See A Recipe For Overpaying for a succinct explanation by Chris Schindler.

7) Takeaway on Diversification for Risk Management: Diversification not only reduces variance drag but also lessens reliance on unpredictable alpha.

🟡Moontower highlight: “Our take away is that idiosyncratic variance drag is much more predictable than expected return. More generally, it is easier to predict variance than mean return. It is therefore safer to diversify more as it will reliably bring down idiosyncratic variance drag compared to concentrating more in a hope of higher alpha.”

 

It’s a love letter to diversification mixing words and math. For what it’s worth, at SIG Jeff Yass also called diversification a free lunch.

I’m partial to my Sun/Rain example in You Don’t See The Whole Picture which is an even stronger statement — you are incinerating money by not diversifying but if you evaluate yourself by “resulting” you won’t see it. That’s because the highest bid for risk is the most efficient at absorbing it. This is deeply true in the derivatives world. In the broader investment landscape it’s confounded by info asymmetry, principal-agent conflict, and the comfort of (perceived) safety in herding.

If you want to get deeper into this idea see the back half of the moontower guide:

🟰Understanding Risk-Neutral Probability (link)

 

But be aware…”diversification always means having to say you’re sorry” since something is always losing.

And sometimes almost everything loses. This was Wednesday. Eww.

 

ETF slop

On the investing front there is an absolute explosion of new ETFs being listed every month.

Dave Nadig gave a presentation for Kitces.com and summarized the key points in:

The ETF Market: A Zine (14 min read)

A few notable takeaways:

  • ETFs have become a behemoth of $10 Trillion in assets across some 4,000 products.
  • That growth has come largely at the expense of traditional active equity mutual funds, although the worst of that outflow seems to have abated a little. As every asset manager on the planet finds a way into the ETF market, the “horse race” between mutual funds and ETFs matters less and less.
  • Traditional Mutual Funds will exist forever thanks to 401ks, or until someone rewrites the entire US retirement system.
  • The industry is on a massive product development binge, launching 650 ETFs this year so far with an open/close ratio of 3:1.
  • Over 40% of industry revenue comes from products that aren’t cheap beta.
  • There are more ETF Brands now then there were ETF Tickers 20 years ago

The post is directed at financial advisors but hands-on individual investors should certainly read it.

And if you’re interested, there is even a “how to launch your own ETF” discussion including a link to Corey Hoffstein’s tutorial.

One of the comments describes the post well:

A wonderfully-written, comprehensive, and refreshing time piece about the real story of ETFs for all – pro’s or not!

All this financial, umm, innovation does get a little chuckle from me (levered exposure to individual stocks? Really? It’s like ghost of single stock futures haunting your watchlist).

The chuckle:

I’m not the only wiseguy feeling this way. This wiserobot is less lazy than me in its skepticism:

The thread continues

Shorting all this nonsense (uncle nonsense reporting for duty) vs going long whatever it’s trying to replicate directly is a labor-intensive way to effectively pay yourself the embedded management fees. But the feasibility is predictably undermined by borrow costs.

But as a trader, it’s a useful reflex to:

  1. Observe the growth of “product” incentivized by fees and lowered barriers to entry
  2. Expect a bunch of trash to be launched with the logic of “it’s a call option on asset gathering”

It can inspire trade ideas from a place of maximal interpretability — you can’t launch all this stuff and expect none of it to be steaming hot turds.

Dave even warns you about what’s coming to the crap carousel:

I have been asked about getting private equity and credit into ETFs every single week this year so far. I’ll just put the marker down here again: this is a bad idea. YES, it is the case that we have broken market capitalism so badly that the majority of what we would recognize as actual capital allocation and risk taking happens privately. NO, that is not a good thing, and it does not mean we should shove all that private capital into daily-liquidity structures like ETFs.

The money currently trapped in private markets is desperate for liquidity so it can invest back into greener deals where there’s more profit runway. That money will push, and push, and push until it finds a new pile of money to sell to. Don’t fall for it. Be super skeptical.

The “world’s worst time traveler” investing style

@lastoneslaughing

#natebargatze #natebargatzecomedy #standup #comedy #standupcomedy

♬ original sound – LastOnesLaughing

 

I’m going to share 2 studies, one new and one old that say something that is counterintuitive to most people but probably not to traders:

Even with perfect foresight of market movements, there’s no guarantee you’ll be a better investor.

The old one first:

Even God would get fired as an Active Investor (7 min read)
via Alpha Architect

This post from 2016. It demonstrates how a hypothetical portfolio built with perfect knowledge of the top-performing stocks over the next 5 years yielded impressive returns (29% CAGR) but also experienced significant volatility and a 76% drawdown.

Even a ‘perfect’ long portfolio can bring a long-only investor a ton of pain.

The hypothetical long/short portfolio, again with perfect foresight, achieved a remarkable 46% CAGR but still faced a 47%+ drawdown.

For investors who are benchmarked the news is still tougher — The god portfolio still underperformed SPY for extended periods that make it hard to stick with.

When a Crystal Ball Isn’t Enough to Make You Rich (20 min read)
Elm Wealth

Victor Haghani and his team discuss an experiment where participants were given historical front pages of the Wall Street Journal and tasked with trading stocks and bonds based on the news.

Hijinx ensue.

The majority of participants, despite having access to “future” news, failed to generate substantial profits. Many even went bust. This highlights the difficulty of translating information into profitable trading decisions. (It’s why opinions are worthless. The question is always “ok, what’s the trade?”)

Notable findings:

  • Trade-Sizing Crucial: The disappointing results stem primarily from poor trade-sizing decisions. Participants often overleveraged, leading to significant losses when their predictions were wrong.
  • Experience Matters: Seasoned traders fared significantly better (they even get a senior Jane Street traders to try it), demonstrating the importance of experience in interpreting information and managing risk.

It’s not shocking that Haghani, one of the principals of LTCM back in the day, reminds us that there is little value in the crystal ball without sensible trade-sizing.

You can try the game yourself:

🔮Crystal Ball Challenge

Haghani is also half the duo behind the famous Haghani-Dewey study where economists and investment folks, many with graduate, degrees embarrass themselves with their inability to size bets on a coin weighted in their favor.

You can play that game too:

🪙Elm Wealth Coin Flip Challenge

My synopsis of it was a very popular post when I published it 2 years ago, (see Bet Sizing Is Not Intuitivebecause the conclusion is profound:

Like these crystal ball/god studies, prediction is just not enough. Betting and trading require a far richer set of practices than just having an edge. Edge is a necessary but insufficient criterion for sustained success.


In the spirit of these games, I’ll remind you of this riddle from Philip Maymin’s Financial Hacking (GOAT-tier trading book — if I’m ever tasked with developing firm or education department this is required reading).

This is excerpted from my extensive guide to the book:

🧩How much would you pay to know the closing price of SP500 in one month?

  • I can tell you where the SP500 will settle in one month. How much would you pay for this information? (And then, what would you do with it?)
  • Let’s say you give a number like $ 10 million, and I accept it. The S& P 500 is currently at 1000. I gaze deeply into your eyes and tell you the truth: in one month, the S&P 500 will close that day’s trading at a level of…. 1000. Oops! Now what? How are you going to make money? You owe me $ 10 million in a month, and I will collect. There is no point in buying or selling futures at the same price at which you expect them to expire. So what can you do? [He doesn’t mention the strategy of announcing your shot on social media and using it to gain followers. The value of this will depend on whether you have something to monetize or follow it up with…and if you do not already have a following it’s likely you don’t have skill in monetizing one so again the value of the follower windfall depends on its beneficiary]
  • All you can do is hope the market moves in the meantime, and it really is a hope, because you have no other information about what is going to happen over the course of the next month, not the volatility, nor the volume, nor the highs and lows. All you know is that it will be at 1000 again a month from now.
  • So how do you time your entry points? Say you have $1 million of liquid assets and say that this much money would let you support up to $10 million in notional, because futures have a haircut of about 10 percent.
  • Suppose you are very lucky and the S&P 500 jumps down to 900 before you even have a chance to put in your order. Now you would want to buy. But how much? Do you put your entire amount on the line, such that even a single tick against you triggers a margin call?
  • Ultimately you can perhaps do best if you are able to buy and sell options, but there won’t always be a liquid options market at every strike you need at the asset that you want to trade, and besides, we haven’t really discussed options yet. [Kris: This is actually the key — you could use options to structure a bet on terminal value but this riddle in general is insightful because it shows just how much you are missing if you don’t understand options]

     

This is the exclamation point on the matter:

These kinds of practical issues are ignored in standard textbook discussions of riskless profit opportunities but they are precisely the issues that financial hackers worry about most. And you will almost surely never experience anything with this level of certainty at any time in your career. There will always be doubts about your model, your inputs, and your forecasts…According to standard theoretical concepts of arbitrage, none of those questions matters. According to real-world practical experience, you can’t even begin to trade until you have answered all of them.

Volatility term structure from multiple angles (part 2)

In part 1 of Volatility term structure from multiple angles we opened by discussing how nearer dated implied vols move around more than deferred implieds. Recognizing that dynamic, our net vega position for a time spread can be ambiguous.

Just as stock traders use beta to normalize risk to a benchmark such as SPX, volatility traders will normalize their vega to a fulcrum month. √t scaling corresponds to a model world where time spreads between months remain relatively stable. It’s not reality but it’s a vast improvement over summing raw vegas.

In comparing vols between 2 months, vol ratios are popular. If M1 is 18% vol and M6 is 20%, the vol ratio is 90%. It’s a measure of how steep the term structure is. If you track the ratio for constant maturities then you can get a quick sense of the relative supply/demand for IV. If the ratio is less than 1.0, the term structure is ascending, a shape typical of “it’s quiet now, but we expect mean reversion to typical higher levels of vol”. A downward sloping vol curve is more closely associated with high vol periods or the market’s anticipation of an even such as earnings or the election.

Vol ratios are only one way to measure the slope of the term structure. We saw that implied forward vols are a complementary measure that also describes the relationship between 2 volatilities on the term structure. The computation tells what volatility is baked into the period between the 2 expirations. The logic is that the deferred expiration accounts for all the volatility from now until the option’s last trading date while the near-dated expiry isolates the early period’s expiration. If you consider an extreme example where the time spread is worth 0, ie the deferred option and the nearer-dated option are the same price, the forward vol is zero.

So why look at 2 measures, vol ratio and implied forward vol, if they both tell us about the relative price of implied vol on the term structure?

Remember, we were looking at GLD 1m/6M vols for the 1-year range 10/2/23-9/23/24:

moontower.ai backend

We saw:

The forward vol is sometimes high and sometimes low regardless of the ratio!

But look at early March — not only was the vol ratio low, the forward got crushed. If you only look at vol ratio, you missed this.

Implied forwards are an orthogonal or complementary measure of relative volatility that is additive to your perspective.

Today, we will dive further into the relationship between vol scaling, forward vols, ratios. We will come out on the other side with what this all means for finding trades and managing risk.

Off we go…

Constant Straddle Spread vs Forward Vol

Suppose you are long a time spread.

We’ll say a straddle spread because that’s a common trade expression and it also connotes delta-neutrality.

[It’s probably helpful in thinking about these things to not have to process “call”, “put”, and their associated directionality. Depending on where you are in your learning I’m trying to be mindful of cognitive load.]

You’re long a 6-month straddle for 15% vol and short the 1-month straddle at 15% vol. Front month vol suddenly spikes a point to 16% and the 6-month vol increases by 1/√t (ie 1/√6) or .41 vol points to 15.41%

Here’s what we know:

  • The term structure went from flat to descending.
  • You lost 1 vol point on your 1-month straddle, gained .41 on your 6-month straddle. Because the 6-month straddle has 2.45x as much vega, you broke even.
  • The straddle spread is unchanged.

What happened to the forward vol?

You can compute it yourself with the moontower calculator but I’ll just tell you…the implied forward vol increased to 15.3%

Let’s summarize what happened:

  • You are long raw “click” vega since you own the longer-dated option
  • You are flat weighted or scaled vega if we use √t scaling with reference to M1
  • Vol across the curve increased in proportion to √t weights leaving the straddle spread unchanged
  • The forward vol you are long increased, although your p/l is unchanged.

The key point to appreciate:

A constant straddle spread price does NOT mean the forward vols are also constant.

Another way to say this:

The same straddle spread price can yield different implied forwards!

 

Implied Forward Vol: a “many-to-one” relationship

For any implied forward vol there are many pairs of vols that can produce it. This is why the straddle spread and forward are not overlapping measures of term structure.

The table shows:

  • many combinations of vols that generate a 15% forward
  • √t or constant straddle spread scaling means the forward is changing
  • The scaling would need to be sub √t (ie more muted) for the forward to not change. If fact, in a vol increase scenario, the straddle spread price would need to narrow for the forward to be unchanged.

Observing GLD vol data for the past year we can see the many-to-one relationship between:

a) vol ratio and forward vol

For any given vol ratio there are many forward vols. It’s not a function.

b) vol pairs and forward vol

For any given forward vol, the 6M vol can be a fairly tight range while the 1M vol could be far above or below the 6M vol!

You can see how the forward vol and the 6M vol are positively correlated. This makes sense — the forward vol is driven by 5 out of the 6 months in the tenor.

You can also see that at low (high) 6M vols the 1M vol tends to be even lower (higher).

 

Linking the scaling relationship to vol of vol

Remember that weighting our vega by month is analogous to beta weighting a stock portfolio. Beta weighting summarizes a portfolios market exposure with respect to SPX or some other benchmark. Looking at raw unweighted vega is like ignoring the relative volatilities between stocks in a traditional portfolio. $1mm of risk in SPY is not the same as $1mm of NVDA.

√t weighting is therefore suggesting a vol of vol with respect to the fulcrum month (in our examples M1). If the back month vol is more volatile than √t suggests than our long straddle spread is long raw click vega AND weighted vega. If M1 vol increases by 1 point and M6 increases by .75 points, than the straddle spread and forward are expanding quickly. The beta of the back month vol to the front is high.

We can regress GLD 6M vol vs 1M vol to see the sensitivity. Remember a sensitivity of .41 would be √t or constant straddle spread scaling.

√t scaling seems to underestimate the beta of 6M vol to 1M vol. A long straddle spread would be long weighted vega not just raw vega.

We can also compute the standard deviation of vol changes to see the vol of vol. You can see that the empirical 6m vol of vol is less than 1M vol of vol (totally expected) but it’s higher than what √t predicts.

If you truly wanted to be flat weighted vega you’d need to ratio the spread to have less units of the deferred straddle.

 

Takeaways and Discussion

Vol ratios are common ways to represent the steepness of a term structure.

A tradeable expression of a vol ratio is the price of a vega-neutral straddle spread (using our example from today, if you buy 1 6M straddle and sell 2.45 1M straddles). Its performance mimics the vol ratio chart at the beginning of the post!

Ratios just like beta-weighting sterilizes a position from the price level to isolate the slope.

You can even track or trade straddle butterflies to bet on the curvature of the term structure.

These are popular ideas from the futures and yield curve worlds:

From that picture you can see how you might not have a strong opinion on A vs C (a slope bet that would be expressed in a ratio trade) but on the curvature between A and C (which would be expressed via butterfly or a “spread of spreads”).

The forward vol is an orthogonal measure

Implied forward vol changes even if the straddle spread doesn’t. We saw the many-to-one relationship between forward vol and the pairs they come from as well as the vol ratio.

💡Aside on Pairs trading💡

We’ve been talking about vol ratios along the term structure but we can combine our use of forward implied vols to inter-asset or pair trades.

In moontower.ai we have this vol ratio tool. Here USO vol looks rich compared to XLE

But you could also compare forward vol to forward vol difference in a matrix view.

These are cobbled together from 2 screenshots but you can imagine a UI which shows a matrix of all the individual forwards. Those implied forward ratios could then be compared to a vol cone of realized vol ratios between XLE and USO.

via moontower.ai

 

The orthogonal nature of implied forwards gives you another set of data to run through all your conventional views to see if something stands out.

I’ve mentioned many times in my writing how I hate vol trades that start with “skew is cheap or expensive”. My experience is that the “skew knows”. It’s highly self-fulfilling. Plus implied skew doesn’t vary as widely as realized skew, so you’re forcing convergence trades on a compressed implied range that doesn’t compensate for how sloppy vol can get on destabilizing moves.

Term structure trades on the other hand. This is the place to look.

Risk limits

Deferred vols are less volatile than near dated vols. It’s important to re-scale the vega per month. √t is as sensible choice as any but your survival shouldn’t depend on any particular choice mattering that much since it will be wrong.

Just as you would never trust all of your delta risk management to the concept of beta, vol scaling weights should be taken with a grain of salt both in terms of modeling changes in term structure and in determining risk limits.

As a risk manager, if you constrain net vega without also constraining gross vega (ie the absolute value of vega within each expiry) you are inviting a situation where a book looks flat based on some weights but masks giant time spreads underneath the surface.

Examining vol of vol directly as well as placing term structures into context with vol cones can offer an ensemble view to understanding how extreme time spreads can get.

 

💡A word on measuring vol of vol💡

In this post, I computed the standard deviation of vol changes. Any experienced trader knows that this is incomplete. Because of spot-vol correlation and skew, vol changes are not pure. They are a mixture of moving along the curve vs the curve shifting.

Always ask yourself — “what measure correlates to how my p/l performs?”. That’s what you care about.

In this case, you want to measure the vol of strike vol not some nebulous concept of floating ATM vol.

 

Extending the analysis

Gold doesn’t typically see much event vol priced into it. Some macro reports like unemployment or key Fed meetings will get their bump in the term structure but it’s not the same degree as say earnings for a single stock or the annual USDA Prospective Planting report in ags like corn and soybeans. These sort of events can can 1 or 2 weeks of vol priced into a single day.

Event variance propagates through the term structure in inverse proportion to the DTE. To say it in friendlier terms…they don’t impact the deferred months much relative to the fronts.

I will re-run all these charts for another name (thinking NVDA) for the past year and see what I come up with. I expect a lower vol beta than we saw in GLD but mostly as an artifact of the near-dated vols having a much wider range because of earnings.

Options Riddle

I saw a familiar type of riddle on Twitter that was directed at fundamental PMs. I gave a lazy answer and later improved it with a better answer after my half-assed-ness gnawed enough at me.

I’ll reprint the riddle and the better answer here but spelling out the steps in greater detail than I did on twitter.

Question:

Estimate the price of a $180 call (20% OTM) on a $150 stock with 50% volatility, 3 months to expiry

150 Call Calculation (The ATM option)

We start by estimating the at-the-money (ATM) call value using:

ATM straddle = .8 * stock price * implied vol * √(Time to expiry in years)

ATM Call = .4 * stock price * implied vol * √(Time to expiry in years)

ATM Call = 0.4× $150 × 50% ×√1/4= $15

180 Call Calculation (The OTM option)

The 150/180 call spread links the 150 call to the 180 call.

Call Spread Value Breakdown

The call spread’s total probability of expiring ITM is around 45%. This is another estimate off the top of my head.

Although you’d expect 50%, option models assume lognormal stock distributions because returns are compounded. Compounded or geometric returns are subject to “volatility drain”— pulling median price expectations lower than the forward price.

You can think of the expected value of the $150/$180 call spread in two parts:

  1. The probability that it expires worth its maximum value of $30. This is P(S>$180)
  2. The value on average when the stock expires between $150 and $180.

    This is 45% – P(S>180)

Computing P(S>180)

Note that the straddle is simply 80% of a standard deviation.

The $180 call is conveniently $30 OTM or .80 standard deviations OTM

We know that 1 standard dev encompasses 68% of a distribution, so at a z-score of +1.0 the one-tailed CDF must be 16%

Spelling that out: 100% – 68% = 32% but we only care about the “up” case when the call is ITM, so we cut that in half to 16%.

Since this exercise is supposed to be all mental math, I’ll guess that a Z-score of 0.80 gives a one-tail CDF of ~ 20%, meaning there’s a 20% chance this call will expire in the money (ITM).

We will assume the 180 strike has P(ITM) = 20%

Expected Value Calculation for the 150/180 call spread

  1. The case where stock > 180

    E(call spread | S>180) = Max value x P(S>180) = $30 x 20% = $6

  2. Case where S is between $150 and $180

    E(call spread | 150<S<180) = Average value of the call spread when s is between the strikes x P(stock between 150 and 180) =

    $15 x 25% = $3.75

    💡Why $15?

    The average roll of a die is 3.5

    The average roll of a die given that the roll is greater than ‘3’ is 5. This assumes a uniform distribution over that range.

    This same style of approximation works well enough for the call spread. Assuming the stock expires between 150 and 180, the call spread is worth $15 on average. The probability it expires between those strikes is the total probability of the stock expiring higher than $150 which I estimated earlier as 45% minus the probability of it roofing above $180 which we estimate at 20%. So the probability of the stock being between 150 and 180 is about 25%

    Hence, $15 x 25%

We sum all scenarios where the call spread expires ITM (ie when the stock is above $150):

Call spread estimate: $6 + $3.75 = $9.75

If the 150 call is worth $15 and the 150/180 call spread is worth $9.75, then the 180 call is worth $5.25

Recapping key bits:

  1. Knowing the ATM straddle approximation .8SV√T
  2. Guessing that the probability of a >.8 standard deviations ~ 20%
  3. Estimating that the probability of the stock going up is less than 50% in a Black Scholes price process (and that at 50% vol that probability is lower than say at 16% vol — in fact the drag is proportional to vol squared)

In the twitter discussion, a great link from 2012 emerged:

Calculating option prices in your head (7 min read)

The Hardy Decomposition offers a handy way to estimate OTM option prices in your head. By breaking down an option’s price into intrinsic value and a HardyFactor (which depends on how far you are from the strike, measured in standard deviations), you can quickly approximate the time value of the option.

The following comes from the post:

Option Price = Intrinsic + ATMPrice*HardyFactor

The HardyFactor is:

d1 is just how many standard deviations you are from the strike.

 

⚠️Looking at a quant forum it looks like the HardyFactor approximation is for options being priced with the ‘normal’ distribution version of the B-S model as opposed to the more commonly used lognormal version

 

Revisiting the riddle

If we revisit the riddle, we know the 180-strike has a d1 = .8 standard devs

If we linear interpolate between .5 and 1 we get a HardyFactor = 40%

Option Price = Intrinsic + ATMPrice*HardyFactor

180 call = 0 + $15 * 40% = $6


My call spread method yielded $5.25

The HardyFactor method (quickly) got us to $6.00

Sound like we have a decent market!

I put into an option calculator:

Pretty fun stuff. If the OTM call IV is discounted by 1 vol point (so -2% skew vs the 50% ATM IV @ the .27 delta option) then the theoretical call value would be $5.616 – .2575 (ie the vega) ~ $5.36


If you want more reinforcement on this I wrote a thorough twitter thread explaining vertical spread comprehension in detail.