Pigs on the Wing: vol tells us nothing about extreme moves

At the close of Friday, I was looking at far OTM gold put spreads.

With GLD at $275, the April 251/249 put spread is similar to a binary bet that GLD expires below $250 at expiry or about a 10% sell-off.*

You get 39-1 odds.

This is using market-based pricing, net of skew.

At-the-money vol is 16%.

Turns out 39-1 is about the right odds if we use 16% as a standard deviation. When I say “about right” I simply mean the gold left tail is basically conforming to an out-of-the-box Black Scholes distribution. I don’t mean B-S is “right” just that the put spread odds conform to what the B-S would say.

I wouldn’t expect that for SPX puts, but gold downside doesn’t have that much skew or tail fatness.

See the table mapping ATM vol relationship to the likelihood of ~10% selloff in a Black-Scholes world:

But a lesson that is far more important jumps out:

Implied volatility—the second moment of the return distribution—has almost no direct connection to the probability of catastrophic price moves!

Look how likely a 1-month 10% selloff is as a function of implied vol. If vol is 15% instead of 12% such a sell-off is 4x as likely and if it’s 18% instead of 12% it’s 10x as likely.

Just think of VIX…it can easily be 12 or 18, right? But what you should really take away from that is that volatility tells us very little about the tails.

Option Pricing on the Wing

 

A few things option traders learn early about pricing tails:

  1. At-the-money volatility tells you nothing about the true probability of large moves.

  2. Tail risks are not just “scaled-up” versions of small market moves.

  3. Historical data is almost useless for extreme events because of sample size is too small to build robust probability estimates.

Instead, traders price tails based on…other tails.

Not backtests.

I invite you to keep your eyes open for sales pitches that pretend they know the likelihood of extreme moves and how they claim to know it. And if the sample sizes weren’t small enough, marketers might try to condition the probabilities — “when the market does X the probability of an extreme event does Y” which reduces the sample sizes even more. Godspeed with analysis that looks like that.

Inferring tail behavior from the meat of a distribution is so sensitive to small changes in volatility — so sensitive that it’s a clue that they’re not strongly related. I’m not making a math argument (I’m sure many readers could say what I’m saying formally). It’s a common sense observation that falls out of the volatility itself being volatile and sensitive to sampling.

The true odds of extreme moves are unknowable but there’s no reason to think they move increase an order of magnitude when VIX goes from 12 to 18, or for that matter, get cut by an order of magnitude when VIX falls from 18 to 12.

*The concept explained in a deeper understanding of vertical spreads

a misconception about harvesting volatility

The final boss of all risk management is position sizing. Whether it’s owning tails, using stops, or hedging with anti-correlated assets it’s all managing your net exposure either locally or to a scenario based on shocking the portfolio.

That’s all delta-hedging to “scalp your gamma is”.

“But Kris, don’t I need to scalp the gamma to isolate the vol of an option trade?”

Technically, no.

By hedging your delta at various time intervals or as your position size breaches a threshold, you are first and foremost reducing market exposure risk. You do this because you don’t want directional p/l variance to swamp the vol-driven reason for doing the trade. A byproduct of this is your hedges “sample the vol”. If you hedge on the close every day and the market always comes back to unchanged after having large intraday ranges, you will sample a zero volatility. If you hedged intra-day you will sample a much higher volatility.

There’s no escaping the reality — every option trader experiences their own realized vol regardless of what the close-to-close volatility says unless they hedge close-to-close. If you benchmark realized volatility as close-to-close, you could think of your sampling as ‘volatility tracking error’ even though there is no “single volatility”.

Your hedges might sample the vol, but the intent is to cut risk, ie manage position size. You can appreciate this by considering the opposite extreme — you do option trades for volatility driven reasons but you never hedge.

What happens?

You are still trading vol. The expirations are the moments when you “sample” vol. The realized vol you experience is point-to-point volatility over longer stretches of time. It’s just hedging on a long interval.

You avoid that strategy not because it doesn’t isolate vol, but because it does so with unacceptable error bars. Remember, hedging is always a cost. It’s the price you pay to reduce p/l variance. If it was anything but that, then you’d have edge on your hedges and you should probably forget the options altogether and just trade deltas like a normal person.

There’s an important implication to this.

You can just trade vol without delta-hedging. To do that, you can just trade much smaller such that the error bars are acceptable. You could still do attribution as if you hedged daily to deduce whether you were doing a good job picking vol longs and shorts, but your actual results will have significant tracking error. If you are a retail trader you don’t have anyone to answer to other than your own tolerance. In Retail Option Trading, Euan explains how he trades straddles and doesn’t delta hedge. He’s not crazy. He’s just trading smaller than he would if he hedged assuming a constant risk tolerance between the 2 possible approaches.

It’s also my approach. I don’t delta hedge my PA. When I put trades on, I make sure I’m comfortable with the notional underlying dollars not just the premium.

If you run a vol business, you want to maximize throughput on your edge to maximize ROI on what you’re good at. This will prescribe delta-hedging. That’s an efficient business decision to give the stakeholders the product they want, even if it costs you expectancy (again hedging is always a cost). But it’s a misconception to believe that you must delta hedge to isolate vol. It’s just that you’ve decided the cost to cut the variance is worth it.

In sum:

  • you are trading vol when you trade options regardless of whether you delta hedge
  • hedging is to reduce p/l variance
  • a byproduct of that hedging is reducing the tracking error to some platonic notion of realized vol (like close-to-close)
  • if the tracking error is tolerable, you can accept more variance, but trade smaller

In a related note, Andy posted:

I’d buy size on that. I wouldn’t consider hedging until I got at least 6 figures of volume on my hedge. But regardless of whether I hedge, I am trading vol.

Moontower Testimonials

Recently, I’ve been fortunate to receive some thoughtful feedback from readers in light of the different modalities (writing, video, app). These testimonials, all shared in the past few weeks, highlight how ideas can connect theory to practice, spark new perspectives, and even accelerate the learning curve for those in the thick of it.

It I was overwhelmed when they came rolling in via quote-tweet, text message and DM after I shared that I got this note::

I need to compile every message where someone tells me about a prop firm telling a junior to go read🌙🗼 .

I never take it for granted that the “stoner dad” letter namesaked by a beer bust scene is read by the hawks of the trading world.

I was in the final round for CitSec and was recommended Moontower as a great read! I have been enjoying it ever since and would love to connect and learn more.

A few replies:

Very flattered to be the contra on these notes I received after that thread:

A Senior Trader’s Take

Originally posted on X by @CedarsHill

“I noticed this post from Kris earlier in the week and it has stuck with me. This is one of the most elegant implementations of Bayesian logic to trading options I have seen in my career. I worked at SIG and learned a lot of this stuff years ago, but it just sunk in at another level.

(Referring to this thread)


From a Young Options Market Maker

“Hey Kris, your recent post walking through the probabilities/‘stabilizing & destabilizing moves’ implied by the NVDA call spreads really stuck with me despite zero relation to the single stocks world, mostly because it felt like a very visual way to grasp the intuition (and I usually suck at this kind of mental abstraction/visualization). Today by chance I was walking through skew on the desk with someone who isn’t really vol savvy (and in a totally different context, FX), and at some point I realized I was mostly borrowing from your logic about how it balances the odds between different areas of the distribution—I could literally see it ‘clicking’ for the guy (and he said so too). And in a way it ‘clicked’ for me too as I went through the concept with these new lens! Figured that was nice feedback to pass along as you recently posted about your work being recommended to juniors and trading desks…I can say from personal experience it would have made a hell of a difference in speeding up the learning curve back when I was in that position.

When I asked the trader if I could share this as a testimonial he replied:

Feel free to share it however u prefer. I can give you the full version of the praise—I’ve been a reader I think probably since year 1 (!), back then I was in my 2nd year on a vol desk (enough so it’s past that point where you feel like everyday you’re fighting not to drown, but not nearly close enough to really ‘seeing the matrix’ so to speak). The stuff you write is literally in the realm of professionals but explained in ways that anyone could eventually understand. There were multiple topics on which I would read your pieces and think ‘ok that condenses in a very intuitive way what I felt it took me many months doing the hard work of trading, controlling position spreadsheets, doing P&L attribution, before figuring out how it really is traded in practice, what are the thought processes, what are the practical pitfalls’. When I started I took the more difficult route of going through the tougher theoretical books first (like Rebonato’s) before getting to the more practical/intuitive ones (like Bennett’s) and before getting to the useful corners of ‘vol twit’ (and then your blog). For someone starting from scratch (and learning on the go) a bunch of stuff was really, really difficult to grasp—Moontower would be literally the first required reading I’d recommend because of this bridge between theory and the practical reality of its applications, there’s really no book or other blog that I know that offers that. For a few years now I don’t deal with vol stuff directly, but once you learn to see the world through options lens it’s the type of thing you can never ‘unsee’ afterwards, and I still don’t miss 1 post.”


From an Option Market Maker with 20 Years of Experience

“These videos are a really authentic sneak peek into the mind of a real options trader, must be neat to watch for people that have never sat on a desk. I watched that first one you posted and your Excel tool reminded me so much of the production pricing and risk management sheet I built over many years and traded off of from xxxx-yyyy.

Your content is amazing, consistently a must-read. So much of it resonates in drastic ways and makes me think hard about my life and my choices (which I already do, but enlightening to hear it framed by someone as thoughtful, humble and self-reflective as you).”

the edge empires are built on

I cleaned up a thread I wrote before NVDA reported earnings Wednesday afternoon. It conveys what I was thinking as I looked at the option surface for the Friday 2/28 expiry.

Thinking aloud as I’m looking at NVDA options before earnings.

My instincts — given the January sell off in NVDA that the stock probably has some discount in the price going into earnings. In other words, if earnings are a nothingburger I’d expect a small rally. No news is good news.

Narrator: I start by announcing my bias. Whether it’s dumb or not is irrelevant. Before you look at a price, chart, option surface you probably have an expectation of what your eyes will see. I probably had many biases. But that one was the most salient before I looked at the option surface.

continuing…

Translating into option speak — the stock is probably going up in terms of “hit rate”.

When I look at the option market, it confirms my bias (not necessarily my reason, but I’m not sure I’ve ever known a reason for anything that wasn’t as tautological as “more buyers than sellers”).

What makes me think the market confirms my “it’s probably going higher” bias?

The downside skew for earnings is fat and the 130/135 call spread is expensive. The market communicates via prices because prices offer odds. You disagree with the market by saying “buy” or “sell”.

How does the price of a call spread tell me anything about the odds?

Start with a simple proposition.

If NVDA was 50/50 to go up or down, you’d expect a $5 wide call spread to trade for $2.50 with the stock at $232.50 which is the midpoint of the strikes.

The stock was $129.50 and the 130/135 call spread was priced around $2.20.

Hmm. Antennae is up.

The call spread has a .15 delta. Meaning if we shift the stock $3 lower from $132.5 to the current $129.50 price, I expect the call spread goes from about $2.50 to $2.05 ( a change of $3 x .15)

So the call spread looks about $.15 rich compared to coin flip pricing.

How do we contextualize how if $.15 in terms of edge?

Well, think go back for a moment and think of the 50/50 case. If the stock was at the midpoint you expect the call spread to be worth $2.50. But if it’s $.15 rich or $2.65, if you sell it what kind of odds are you getting?

You are risking $2.35 to make $2.65 or getting 1.13-1 odds. What does a bookie give on an even money bet? 110-100, right. Empires are built on less edge. $.15 is a lot of edge on a $5 wide call spread.

[Personal opinion interlude: I think this was the biggest insight SIG conveyed to us when I started in the biz. Markets were wide when I was in training and you could get that kind of edge on benign things like call spread. SIG had a reputation for trading big. Using their capital, we were told to get as many lots as we could on every trade. You’re job was to fight for large allocations or splits. The edge compared to the risk on these things was much larger than the edge they saw gambling operations compound on so they optimized for market share. Many less-capitalized firms wanted to maximize edge per trade, which meant they were reluctant to tighten for market share, which can be the right move if you’re undercapitalized.

We were trained to be pigs because they understood that the getting was way too good to last so you want to maximize p/l, area under the curve. So you often pissed everyone off. Our nickname on the floor was “evil empire”*. When you start out you’re reassured “oh, it’s because we wear the black smocks”. But you learn that it’s because we acted like Amazon in a world that still had lots of indie bookstores. You can level whatever you want against Amazon, and they’ll just say “it’s better for the consumer”. Of course what they also mean is — “scoreboard”.

E-commerce and trading are bloodsports. As you learn in trading, in 5 years, you’d kick a grandma down the stairs for the thin margins you’re complaining about today. If you’re young and reading this, the cycle I’m describing is evergreen. There is someone willing to physically fight for your job if you are in a seat with an edge. That you don’t see a fist swinging at you doesn’t mean you’re not in a conflict. The zero-sumness of prop trading is the animating force behind its evolution. If that sounds rough perhaps you’d prefer a career in asset management where “solutions” can be customized to a client’s frontier. Also, if what I’m describing makes no sense to you or sounds dramatic…you’re not in trading.]

Back to the NVDA call spread…

What was my thinking and what did I do?

I didn’t trade it.

I did not sell the call spread that looked expensive. The vol lens said it was expensive, but the prior I had, “the stock is probably going a bit higher” was baked into the option market. If my prior no news is bad news, then I would have sold them.

[Note that the prior is playing a real role here and it was based on vibes. This is a complicated matter. On the one hand, I know why I give weights to my prior. It’s an old habit, that was justified. Was.

In a trading seat, you ingest a lot of unstructured flow data. Which brokers bid or offered a particular option in size? Maybe they passed. Maybe they checked another strike. Why that one? How aggressive were they, have I seen the signature of this flow before? You’re always playing this little deduction game and its output becomes the priors that influence positioning.

Today, I don’t get the same context. It makes me more hesitant. It makes me give more weight to implied odds versus my prior. In fact, with a liquid name like NVDA there is so much electronic flow that perhaps the option surface odds simply reflect a risk premium. Maybe I shouldn’t read too much into the implied odds of earnings call spread and just accept it as the price to clear a flow imbalance as opposed to anything deserving predictive weight.]

Finally, I believe the contrarian trade is probably to spec some way topside call or call spread because that’s the most discounted part of earnings. Probably for good reason, but that also means it’s the more “destabilizing” move. You only get nitroglycerine if everyone is offsides.

The main lesson:

Unlike myself, many of you have stronger conviction stock opinions, so I hope marrying it with what the options market is offering allows you to better pinpoint how you should express them.

🔗Further reading to that ends

 

*Like these guys, I’m an Empire enjoyerrrrr

So much so that I wore a Queensryche shirt when Matt had me on his show.

But I also couldn’t decide which old school empire reference to use so you get my other favorite:

Honorable mention:

Evil Empire - Rage Against The Machine ...

Benn Eifert returns to Odd Lots

QVR’s Benn Eifert continues to be the best translator of options to normie speak. All of his podcast interviews are full of useful knowledge about options and asset management practices.

His latest appearance on Odd Lots is no different.

I excerpt my favorite parts with my emphasis at times.

1. Buffer ETFs and the Related Structured Product History (UConn Story & Cost of Predictability)

Question: I saw a headline float by about the University of Connecticut’s endowment dropping some of its hedge fund exposure in favor of buffer ETFs. What are buffer ETFs?

Benn Eifert: “So this is a big new manifestation of a relatively old popular idea. So buffer ETFs are usually pitched as sort of defined outcomes in some sense over some time period where they say, well, what you’re trying, what we’re trying to do is give you equity exposure, but you have protection, you have a buffer down to say 10 or 15% where you’re not gonna lose money as the market goes down. And then beyond that point, you’re exposed. And in order to do that, you’re gonna sell an upside call, you’re gonna give up some of your upside. And so what this is, it’s basically just a put spread collar, which is a very standard kind of option structure where you sell a call to buy a put spread that is for many, many years and decades by far the most popular thing that a Wall Street derivative salesperson will run around trying to pitch to their clients.”

One thing I don’t get is like, why would you prefer doing that versus just buying a bunch of equities and maybe hedging in a more traditional way like buying some bonds?

Benn Eifert: “So this is exactly the right question. So the first thing that, you know, a derivatives person looks at when you look at a trade like this is, okay, what does this do to the delta, the equity exposure of your position, right? So if you buy some equities, that is a one delta—a derivatives guy would say it’s just a delta one position. Market goes up a percent, you make a percent. If you trade a typical put spread collar against that, you buy a put spread, you sell a call, you’re probably gonna take that one.

And so if you do that kind of a trade, you might take your one delta option down to like a 0.6—down to a 60 delta. So now you’re only participating kinda 60% in the movements of the market. And if you look at how these kinds of trades perform over long periods of time, they actually act a whole lot just like having sort of 60% as much stock, right? Because ultimately they’re rolling these—it’s not really like a buy-and-hold-to-maturity thing. It’s like they’re rolling these options to kind of maintain this kind of exposure. And if you were just to take the counterfactual, which is why don’t I just own 60% as much stock and put 40% of the rest in T-bills? Turns out your fees are way less and your performance is probably better.”

Are there institutions, you know, Tracy mentioned the University of Connecticut… are there certain types of institutions where this is in alignment with the institutional mandate?

Benn Eifert: “So there are cases when that’s to some extent true, at least with some kinds of derivative structures. So you’ll have cases where there’s like a big disbursement that has to be made at some future date and they wanna lock in for sure the fact that they can make that disbursement, but usually something more like an outright put is gonna be a better match for that. Right? ‘Cause the thing about the put spread or the put spread collar is you’ve only got like this say 10% buffer of protection, and what if the market crashes?”

So this, if the stock falls or if the market falls 25%, which does happen, you are actually not protected against all of that.

Benn Eifert: “Yeah, exactly right. Yeah. So this stuff really doesn’t lock in defined outcomes to the downside. It just gives you kind of some buffer of protection in exchange for some upside that you’re losing.”

You touched on this earlier, but talk to us a little bit more about the commissions and the execution and whether or not you’re getting a good deal on those.

Benn Eifert: “Yeah, no. So this is a really important point. Generally, these are not always, but typically these kinds of structures exist in fairly popular, fairly liquid underlyings, right? This isn’t like micro-cap stocks, this is S&P or something. So the bid-offer spreads don’t look that wide when you look at it. But you have to keep in mind if you have a $22 billion fund that once a quarter is rolling this giant collar and everybody knows about it and knows exactly what you’re gonna do and knows exactly when you’re gonna do it, then obviously the market just moves right ahead of you, right? And everybody positions for this trade that you’re gonna do.

[Moontower take: this is well-aligned with my broad view that the inputs into an option price mean they are surgical tools — they are highly levered to the specific inputs. Strategies which use them with little discernment as a blunt instrument are poorly matched to why they’re useful at all. I wouldn’t die on that hill because I can imagine a very good argument for using them in a systematic way but the details matter and my point would be that the argument would indeed need to be very good to overcome my prior. The hooker asset management world often just sees a new trick where they can hide behind “I’m giving the customer what they want, that’s capitalism” but generating demand by playing framing games is zero-sum. Of course I’m biased, every time a person who makes their money in marketing outbids an option trader for a house my pen gets saltier.]

2. Benn’s favorite blow-up story

I think possibly my favorite was Allianz’s Structured Alpha, which blew up in 2020 in March. And the reason was, you know, Allianz is a huge sort of safe conservative firm that everybody would look at and say, ‘Oh, they would never be doing something kind of crazy, right?’ Because it’s, you know, they’re very buttoned up, they’re very serious people. They own PIMCO, and so they—but they had these French kind of option traders…”

(Joe Weisenthal chuckles at “French.”)

Benn Eifert: “Yeah, it’s always the French. There’s just something in the DNA.”

“And, you know, they were doing something where they would effectively, they would usually sell downside put spreads—they’d sell a put, and then they’d buy back a lower strike put. That was the main thing. They’d do a few other things, but like, think of that as the core thing they were doing. Right? And that’s kind of safe-ish, right? You’re getting some credit, you’re earning some premium, but like, you’re supposed to know how much you can lose.”

“And then—but the returns were pretty good. They actually kind of kept up with equity markets, which doesn’t really make a whole lot of sense. And it turned out the way that they were doing that was that they were just not buying back the downside put—or they were buying it back but like way, way, way lower strike than they said they were buying it back.”

Joe Weisenthal: “Oh, that sounds really bad.”

Benn Eifert: “Yeah, that was really bad. And they were doing that for years and years. And it’s actually really great—there’s a whole SEC complaint about this. You can read all the details. They had to show this to investors, what they were doing, right? Because that’s part of the business. And so they had spreadsheets with all these hardcoded cells and made-up numbers to sort of be able to lie to investors and say that they were doing what they said they were doing, when they weren’t.”

“And because that’s complicated to manage—to have all these big spreadsheets faking your returns and faking your risk and everything—they actually had a Word document with an 18-point list on how to do all of the lying for all their analysts to be able to follow. And, you know, instructions on how to not hover your mouse over a formula… because the investor might see that the number was hardcoded instead of a formula.”

“They didn’t have some sophisticated methodology for this. They literally just typed the numbers into the spreadsheet.

Joe Weisenthal: “You don’t even need to be French to do that.”

Benn Eifert: “That’s right. You just go to cell C6 sometimes and you just overwrite the number.”

“So what happened was they sold lots of VIX calls with the front-month futures at about 25. And then the front-month VIX futures went to 85. And so they were liquidated in the middle of March in a huge catastrophic explosion that people like us were shown in an auction and everything. And they drove the relative price of VIX options and futures to twice as high as it had ever been relative to S&P, in this sort of spectacular implosion.”

“They went to zero. They lost billions and billions of dollars for teachers’ pensions and all this kind of stuff in just total and utter fraud. Again, at a very big buttoned-up place.”

“And actually, one of the funny takeaways from it was, in all of the lawsuits, you know, Allianz stepped up and settled lots of lawsuits and paid investors back—you know, all this money, and it cost them many billions of dollars. And so actually, in a twisted sort of way, the logic of investing with the big safe place actually worked but it wasn’t because they managed the risk or had any idea what these guys were doing. It was just that you could sue them, and they would pay you.

3. The History of Option Selling: Good Until It Got Popular

Benn Eifert: “So from 1990 to about 2012, they look pretty good. They kind of keep up on average with the S&P but on somewhat lower volatility with a little bit lower drawdowns.”

“Option selling looked good when nobody was doing it in size, right? Option markets were a backwater. There were funny little things that a few hedge funds did, and a few kind of people, but there were no giant pension, $200 billion pension funds doing option selling. And then those pension fund consultants started writing white papers and they started pitching to their clients’ boards, and by like 2011, 2012, 2013, they started to get some traction. And you started to have, you know, giant $200 billion pension funds saying, ‘Sure, we’ll put 10% of our assets in, move it from equity into option selling.’ And that grew and grew and grew and grew and grew.”

“And what happened was you see that performance then—in kind of the out-of-sample period, if you wanna think of it that way from a back test—yeah, for BXM and PUT index, which are the benchmarks for this kind of stuff, then really deteriorated relative to S&P where they sort of had very similar risk but much less return.”

4. How to Start Using Options Carefully

Benn Eifert: “Usually the first thing that I do is I send people a thread that has a collection a lot of people contributed to on good reading material and stuff.”

“And then, you know, the next thing that I tell people is what do I think are kind of reasonably safe uses of options that if you really want to dedicate time to figuring this out, you might kind of start with, right?”

“If you want to be really thoughtful about options selling, you know, to try to generate yield over time, there’s ways to do that too. But you really have to read up to understand how to think about the risk-reward of a trade that you’re doing—not just believe there’s something you can do all the time because somebody told you it’s a great idea.”

if you have a low rate mortgage, you incinerate money when you sell

This post is an excerpt from the finance part of why home prices could fall with mortgage rates

I extracted it because it is a tidy explainer of something you feel but might not be able to articulate.

The reason you feel that selling your home to buy another these days feels like you have somehow incinerated money, is because you are.

It’s just bond math — you are buying a loan that is trading at a massive discount back for par when you pay off your mortgage. We can compute just how much money you are incinerating.

Quite unfortunate because along with low-supply and bottlenecks this is financial force that also conspires to remove supply and liquidity.

Excerpt below…


Houses are worth very different amounts to existing homeowners vs buyers. And since many buyers are homeowners (I’m talking about people changing primary residence not second homes), the split valuation even exists within the same brain. You’re Hyde when you list and Jekyll when you bid.

Let’s walk through it.

Homeowners who secured low-interest-rate mortgages years ago effectively “shorted bonds”. As interest rates rose, the value of these loans plummeted, embedding equity into these “short bond” positions. This means that the mortgage itself has become an asset that is highly valuable to the current owner. It’s like “it’s equity in a mark-to-theo short”. But that equity is trapped. It’s specifically tied to that home. The new buyer doesn’t get it because they must finance at the higher current rates.

This mechanically alters fair value of the asset depending on who owns or doesn’t own it. The homeowner might not be able to articulate it but they have two assets: the physical home and the valuable low-interest-rate mortgage. If they were to sell the home, they would have to buy back the mortgage at its face value, rather than its current impaired value thus losing the accrued profit from the “short bond” position.

Let’s make it concrete with a numerical example.

You bought a $500k house 5 years ago with a $100k down payment. You borrowed $400k at 3%.

What do you owe today?

Step 1: Calculate the Monthly Payment on the Original Mortgage

The formula for the monthly payment of a fixed-rate mortgage:

Where:

  • M = monthly payment
  • P = principal loan amount = $400,000
  • r = monthly interest rate = 3%/12 = 0.0025
  • n= number of payments = 360

Monthly payment = $1,686.42

The mortgage still has 25 years (or 300 payments) until maturity.

The remaining balance after 5 years is $355,625 (from this calculator)

In our fake world that’s pretty similar to the real one, a lot has changed in 5 years. Interest rates have doubled to 6%.

What is the value of the outstanding mortgage?

Step 2: Calculate the Present Value of the Remaining Payments

We need to find the present value of these remaining payments, discounted at the current 6% market rate.

The formula for the present value of an annuity is:

Where:
  • M = $1,686.42 (monthly payment)
  • r = 6%/12 = 0.005 (new monthly interest rate)
  • n = 300 (remaining payments)
PV=1,686.42×[1−(1+0.005)−3000.005]

PV = $261,744

The present value of the remaining ~$356,000 mortgage, when discounted at the current 6% market rate, is approximately $261,744.

This significant difference highlights the additional equity embedded in the homeowner’s “short bond” position due to the lower interest rate. The homeowner has an intuitive sense that they are losing when they sell the home because they will have to pay the bank $356k to close the loan when it’s only worth $262k. Eww.

The additional $94k of equity that the homeowner has at prevailing interest rates represents almost 20% of the value of the $500k home!


If mortgage rates fall, the conventional wisdom that marginal demand to buy should increase is a fair assumption. However, rates falling cuts directly into this shadow equity that owners feel compared to a high-rate environment. I suspect this will actually “loosen” a bunch of trapped supply as the bid/ask spread narrows as the homeowners embedded equity in their “bond short” shrinks.

[I’m using the word “shadow” but it’s quite real vs the alternative of buying the same house for $500k at the higher interest rate. It’s “shadow” because the only way to monetize it is to let time elapse until the mortgage eventually goes away. Your lower cost of living relative to someone who doesn’t have a low interest-rate mortgage on the same property is the only way to realize the equity.

Active solutions to this illiquidity trap is allow homeowners to somehow port their mortgage to a new property or allow them to buy back their mortgage at the current value instead of the remaining principal amount.

I already hinted at a passive solution. Let the clock run. As time progresses, homeowners continue to pay down their mortgages. With each payment, the principal balance of the mortgage decreases, and the equity in the home increases. Over time, the impact of the low-interest-rate mortgage diminishes as the remaining balance shrinks. This gradual reduction in the outstanding mortgage balance reduces the value of the “short bond” position, making it less of a factor in the homeowner’s decision to sell. Eventually, as the mortgage balance becomes smaller relative to the home’s value, the embedded equity becomes less significant, narrowing the bid-ask spread.]

If mortgage rates fall in concert with the economy and employment weakening (pretty standard backdrop to falling interest rates), then supply may loosen in combination with general demand shortfall. It feels like a downside risk…but by now I’m also resigned to believing home prices won’t fall. We don’t have enough of them. Lending standards are conservative. There’s nothing frothy about the supply/demand balance. At the same time, it’s illiquid and unaffordable. My selfish position is I’d like to see prices ease but I’d happily settle for a wider selection of homes, even if they are overpriced.

a sense of proportion around skew

Last week, we launched the Portfolio Visualizer in moontower.ai

It’s a tool for using vertical spreads to make directional bets.

Input: You enter a target price and expiration

Output: It shows you a matrix of every out-of-the-money strike combination up to the target in terms of what odds it pays.

A quick refresher on the utility of vertical spreads

I’ve written a lot about them but as a refresher, vertical spreads are clean ways to bet on a terminal price by a certain date.

  • You know your max downside so you can put them on without worrying about being shaken out of them by marks. I call this “risk budgeting” a trade
  • Spreads, especially tight ones, have largely offsetting greeks. When you use an outright option to bet on direction you are expressing a view on a basket of parameters in addition to direction — most notably volatility and its doppelganger time. You can be right on direction and wrong on the other parameters. Using options demands a view on volatility (ie the “volatility lens” I’m always droning about). Vertical spreads discard this requirement because the vol and time exposures are heavily neutralized.

The fussy reader will raise their hand, as they should.

“What about skew?

Doesn’t the implied skew impact the vol differential between the 2 strikes of a vertical spread?

How do I know if the odds are a good deal?”

These are awesome questions. Let’s get to work.

The goal: develop a sense of proportion about how much “high” or “low” skew impacts the odds

Payoff Visualizer

Let’s start with some odds.

We’ll look at the payoff odds for call spreads on SLV and USO etfs on trade date 2/25/2025.

We are looking at approximately .50d – .25d call spreads for expiry 4/17/2025.

In other words, buying roughly an ATM call vs selling a .25 delta call expiring in nearly 2 months.

SLV

Lower strike: $29.50

Lower strike implied vol: 24.9%

Higher strike: $32

Higher strike implied vol: 27%

Measured skew = .27 / .249 – 1 = +8.4% premium

The call spread is marked at $.57 vs a maximum value of $2.50 offering 3.4-1 odds if SLV expires above $32.

moontower.ai

💡Note that if the 32 strike’s implied vol increased, all else equal, the spread would decline in value, the skew premium would be higher, and the buyer of the spread would get even better odds. It seems counter intuitive but by increasing the skew and pumping up the 32 strike call, the market is saying 2 things at once:

  • the magnitude of the upside of the distribution is fatter (the call is expanding in value)
  • the probability or hit rate of SLV going higher is lower — you are getting better odds to be long this binary outcome

This seemingly offsetting sentiment makes sense. If the upside magnitude is higher AND the hit rate is higher then the stock price must also be higher. But if we hold the stock price constant and just move the implied skew, then we are adding clay to the middle & downside of the distribution AND the further upside BUT removing it from the nearer upside.

In sum, silver has positive call skew and the .50d-.25d call spread with 2 months to expiry offers 3.4-1 odds.

Now let’s look at oil.

USO

Lower strike: $76

Lower strike implied vol: 27.9%

Higher strike: $81

Higher strike implied vol: 26.9%

Measured skew = .26.9 / .279 – 1 = -3.6% discount

The call spread is marked at $1.59 vs a maximum value of $5.00 offering 2.1-1 odds if USO expires above $81.

moontower.ai

🔬What you should notice

USO vols are similar to SLV but the call spread .50d-.25 delta call spread is much more expensive (and pays less than 2/3 the odds of the SLV call spread). Skew is driving the disparity. In USO’s case, you are selling the topside call at discounted IV to ATM, but in SLV you selling a premium IV.

Weighing in on whether this is a structural mispricing of the probabilities is not where this post is going. That’s more of a research question. Knock yourself out, if you want to dig up the empirical distribution of returns. I can point to reasons why the skews look like this.

1) Spot-vol correlation

SLV vols tend to increase as silver rallies. Part of the precious metals as risk-off, fiat hedge rubric. Oil is a risk-on asset usually with demand for energy correlated with global demand growth. Like stocks, it has a negative spot/vol correlation. However in times of middle east geopolitical stress the spot/vol correlation can flip to positive.

2) Hedging

Producer hedging in oil markets tends usually involves buying puts or put spreads and selling calls. While consumers (ie airlines and refineries) are natural buyers of oil, their hedging requirements are typically swamped by producers.

[The vol inclined reader will notice that these reasons explain the skew but don’t rule out the call spreads being mispriced. The implied skew reflects the supply/demand for vol at various moneyness, but that’s not the same as saying the implied skew predicts the distribution. If you want to bet simply on directionality in a given time frame, taking advantage of the skew is a perfect use case for the risk-budgeted vertical spread. If you are not dynamically hedging, you are not concerned about the conditional behavior of vol as spot moves around.]

The key lesson of the discussion so far:

The level of skew, the percent premium/discount, is a major driver of the vertical spread price and therefore the payoff odds and implied probability.

An inferred lesson, that is not really surprising, is that different assets have different skews. Nobody is ever going to price a SPY surface with silver skews. Both the distributions and spot/vol correlations have different properties.

To develop a sense of proportion around how the range of measured skew affects payoff odds requires looking at assets idiosyncratic skew behavior. In moontower.ai, we display both time series for skew parameters as well as percentiles

Between knowing if the skew is “high” or “low” compared to history and seeing the payoffs in the visualizer we come to a practical questions that tie it altogether:

If .25d puts are in the 10th percentile vs the 90th percentile, how much is that going to change the odds offered on my put spread hedge?

If skew is at “average” levels what kind of odds should I expect on a 2-month .50-.25d call or put spread?

The remainder of the post will dive into these questions so you can walk away not only with a sense of proportion but be able to form your own rules of thumb so you can quickly handicap values like how much extra your paying for a put spread when skew is “low” or how much more your getting for selling a call spread when the OTM calls are cheap?

Here’s a few thoughts for everyone before we get to the paywall:

1) Tradeoffs

For a directional bet, I don’t really see which spread to buy as a question of “what’s optimal?” You’d need an very fine-grained view of the distribution to identify that. Instead, I see a menu of tradeoffs between hit rate and payoff which the matrix displays naturally. In fact, just looking at the screenshots above of the matrix is very educational.

The matrix is the view I’d construct ad-hoc when I want to take a shot. I didn’t map the whole thing but I’d I basically run the same payoff calculation in my head by eyeballing a bunch of strikes, perhaps according to which option markets were tightest or have meaningful OI for liquidity purposes. It makes life easier to just have it organized in a matrix this way.

2) The hips and the fist

In any fighting sport you learn that power comes from the hips. The fist is just conduit that channels the power. When thinking about a directional bet, the work really is upstream of the options. The options are just the fist. It’s the easiest part. Most of the alpha power comes from the directional analysis. Or sticking your finger in the air.

Developing a sense of proportion about skew

We need to do 2 things to answer the practical question of how much does “low” or “high” skew in name change the value of the vertical spreads in real-life:

  1. We need to see how much skew varies in a name
  2. We need to run extreme skew parameters thru an option pricer to see how the spread’s price range (and therefore payoff odds) varies with the skew parameter’s range

Skew Variation

I did a small study of 3 names with different skew properties. I looked at 3 years of data to find the .50d IV as well as the .25d put and call skew parameters for options with about 2 months until expiry.

🗒️Notes on method

a) I allowed a tolerance of 50-70 days until expiry (that means there wasn’t necessarily a qualifying expiry for each trade date but there’s enough data points to get the gist).

b) Skew parameter = .25d IV / .50d IV – 1 … you can interpret that as a percent premium or discount to the .50d IV.

If .50d IV is 30% and the .25d put is 33%, then skew = +10%

💡Sometimes you’ll hear the term “clicks” or “vol points”. In this example, a 10% premium corresponds to 3 vol points or clicks.

Let’s just jump to the data which I think is mostly self explanatory now that you know the definitions. For each name I show the scatterplot of skew vs .50d vol level for:

a) .25d put

b) .25d call

c) .25d put – .25d call risk reversal

Remember unless it says “clicks” the skew parameter is in percent of .50d IV

USO

QQQ

SLV

Substack’s not the greatest for delivering these charts but you can always right click on the image and “open in new tab”.

The charts are nice because you can see that skew can vary with vol level. That’s discussed in the “key observation” stickies. Those stickies also show how skew is not some abstract idea — its specific behavior matches the specific properties of the underlying asset. Sometimes oil panics up or down. The tech index doesn’t panic up (even if single stocks in the index might).

We can get lost in reflecting when our goal was to see how much the skew varies in a name. This table will make it clear:

We can ignore the risk reversal. I included it because it took no extra effort. Instead, let’s focus on .25 skew. Again, just eyeballing, we can see that the interquartile ranges for put and call skews are typically around 5% wide (silver is a bit wider). Meaning that from the median to the 75th or 25th percentile you are only talking about changing the OTM option’s IV by about 2 or 3% of the .50d vol.

So if median put skew in QQQ is 16.2% premium to .50d IV and skew blows out to the 75th percentile than it goes to 19% premium.

If QQQ ATM vol is 20% your talking about a put IV going from 23.2% to 23.8%

How if QQQ IV is in the 25th percentile?

If ATM vol is 20% then the put is 13.3% premium or 22.7%

If skew went from the 25th percentile to the 75th, the put vol increases from 22.7% vol or 23.8% or just over 1 click.

Is one click a lot?

That’s the question we’re after.

Put spread sensitivity

We can test this using a Black-Scholes calculator.

We can compute a 60 day .50d put at 20% IV vs a .25d put at 22.7% IV.

This represents “cheap” put skew in the 25th percentile.

We will do this on a hypothetical $100 stock.

The .50d put will be actually be in-the-money slightly as opposed to at-the-money.

[See Lessons from the .50 Delta option for an explanation]

We end up with the 100.50 strike vs the 94.50 strike. This $6 wide put spread represent the .25d wide put spread.

When the skew is “cheap”, the IV differential between the strikes is 2.7 vol points (ie 22.7% – 20%).

The put spread is worth $2.03

[The 100.50 put is worth $3.50 and the 94.5 put is worth $1.48]

If we raise the skew to the 75th percentile, the 94.5 put goes to 23.8% IV and a price of $1.62

The put spread drops in value to $1.89

Again, notice when the put skew expands, the put spread drops in value! The left tail is getting fatter but the intermediate down move is losing distributional mass.

This is the put spread as a function of the vol differential between the 2 strikes. As the differential widens (the smaller put increasing relative to the .50d put) the spread gets cheaper.

What happens in odds space?

If the put spread is $2.03 and can be worth as much as $6.00 a buyer is getting 1.96-1 odds.

When the put spread gets cheaper, the buyer gets better odds of 2.17-1

In probability space, you go from 33.8% to 31.5% probability of expiring lower by expiry.*

The put spread changed in value by about $.15 on a $2 put spread as skew went from the 25th to 75th percentile all else equal. Given the variation of skew in QQQ it’s like every 3 cents in the put spread is 10 percentile points.

I won’t step thru it as slowly as I did with QQQ but here’s oil put spreads varying from 5% to 10% to 15% skew for the 100-91.5 put spread (.25d wide put spread):

 
$8.50 wide put spread

Context is everything

When I was trading oil, a giant move in skew would mean, on a delta-neutral basis, a $5 wide spread would move 3 cents. If you made a nickel wide market on a put spread you’d be accused of making a market the broker could “drive a truck through”. In percentile space, you can see why.

But then again, you could argue that the exchange fees and broker commission represented a few percentile points.

If you are an options market maker, translating what low or high means to actual prices is important. It gives your market width context with respect to the surface parameters that you track. It lets you estimate how much edge you need to pad your market compared to how wrong you can be about how the surface might reprice.

On the other hand, if you are a purely directional trader the the difference in skew being low or high might be immaterial to your decision to take the odds unless your are able to discern probabilities down to just a few percent.

Now when you see a skew time series for a fixed maturity you know you can put the parameters in an option model and see just how much it changes the spread value.

You can derive your own sense of proportion customized to the context you trade in.


I’ll wrap by emphasizing that I’m writing from the perspective of mapping skew parameters to actual spread pricing. Trading skew on a delta-neutral basis because you think realized or implied vol will out or underperform as spot price travels across various strikes is a different animal. That is less about distributional outcomes and more about dynamic vol behavior. You care about what IV does when your vegas expand and contract, and what realized does as spot moves through your dollar gamma profile. It’s highly path-dependent. The opposite of a terminal risk-budgeted bet. In fact, the 2 different approaches can prescribe opposite trades meaning the risk-budgeted trader and the dynamic hedger can happily trade with each other. A classic example is the 1×2 ratio spread. The directional trader might use jacked put skew to buy a 1×2 put spread creating a highly attractive payoff profile in most scenario, while a dynamic hedger might be happy to own the 2 options because they expect vol to scream higher as the stock goes down.

For fun: What the most you’d be willing to pay for a $15/$10 1×2 put spread? The least? If you paid zero for it, can you lose?

Update 8/2025:

I was asked if I had written anything on the impact of events on skew percentile measures in the Discord. Sharing widely:

I haven’t, but most events are just one-day pricing problems. The effect of skew from 1-day pricing is heavily diluted if you are looking at 1-month skew and beyond. If you are looking at percent skew in like 1 week options, well all kinds of measurement issues anyway:

  1. IV on 1-week options alone is a hairy topic since assumptions about how much vol time remains become impactful. Which is why if I’m trading near-dated, I really just think in terms of straddles and the price of vertical spreads. For the latter if a stock is trading 102.50 with 3 days to expiry you simply ballpark that the 100/105 call spread should be about $2.50 which is about the same saying the 105 call and the 105 put are equal (HW: prove this with put-parity). All the weird lognormal Black-Scholes math really melts away in the short term and you are in the realm of common sense handicapper.

  2. The vega of options gets small in near-dated options so…maintaining a sense of proportion if important. If the ATM vol is 20% and the skew is 10% (ie 22 vol) vs 15% (23 vol) and the vega is 0.005 you haven’t even changed the value of the vertical spread by a cent even though the skew is 50% larger. I have written about this “sense of proportion” stuff. People get caught up in metrics that when you translate back into price space matter on the order of “it’s like paying an extra commission charge to IB on the trade”. In other words, if the difference changed your decision to trade, then the rest of your infra better be medical grade accuracy bc you’re trading for slivers.

we’ll all be selling placebos in the future

A theme that’s weirdly come up in a few unrelated private conversations with various tech foIk is how it will become very difficult to make money in the future. Like the meme that says you have 2 years to get rich because by then anything you can imagine will be solved with compute (ie electricity) and therefore capital. Labor will be worthless.

It’s a comically reductionist view but its directionality occupies a pied-à-terre in my brain. It’s a messy mental apartment. The thoughts are scattered:

  • I remember when the threat of mass automation was contained to autonomous driving. “Truck drivers should learn to code”. Now it’s the hair stylists who are safe (at least until literal robots take over) and everyone with an email job looks cooked. During covid, I wrote about how it felt so unjust that high-paid workers who sit behind a screen not only kept their jobs but thrived while anyone on the front-lines of humanity got ravaged. It was a deeply regressive crisis. At least an EMP tragedy would have been progressive. It looks like the universe now wants to atone for its prior path.
  • Interest rates, stocks, and home prices are all at their generational highs. But odds are if you read this letter you live in a town or city where the median homeowner affords their 7-figure mortgage with a W2 email job. If automation is deflationary are the most widely held assets entirely mispriced?
  • Is the correct game theory response to loot institutions, pump bags, and discount the value of reputation? Are long-term thinking and “compounding” overbid ideas? (I don’t live as if they are because to believe this requires sociopathic nihilism but I weren’t being paranoid about being sucker I’m probably blind.)

     

I’m harboring all these strange notions. Then, as an example of confirmation bias in real life, Liv’s tweet interrupts my mindless scroll.

 

My interest in the tweet is the part which gestures at market efficiency — “better than any human at maximizing their own capital”. It echoes the theme I opened with — that acquiring substantial capital in the future will become nearly impossible against a master robot race.

(The whole part of creating a human-centric economy is really about political choices. Issues like H1B visas, maternity leave, or how the tax code treats various forms of incomes/costs are the rules upon which American capitalism rest. These are democratically determined even if markets themselves are not democratic consensus mechanisms. That’s not the subject of my musing.)

So this skynet stuff is just floating around my consciousness, then I hear something that sparks a total right turn (not a 180° to be clear). I’m driving back from Placerville last weekend (strongly recommend Marshall Gold Discovery State Historic Park!) listening to Dwarkesh’s recent interview with “two of the most important technologists ever, in any field”, Jeff Dean and Noam Shazeer.

[Some background on them:

Jeff Dean is Google’s Chief Scientist, and through 25 years at the company, has worked on basically the most transformative systems in modern computing: from MapReduce, BigTable, Tensorflow, AlphaChip, to Gemini.

Noam Shazeer invented or co-invented all the main architectures and techniques that are used for modern LLMs: from the Transformer itself, to Mixture of Experts, to Mesh Tensorflow, to Gemini and many other things.

We talk about their 25 years at Google, going from PageRank to MapReduce to the Transformer to MoEs to AlphaChip – and maybe soon to ASI.]

Most of this interview was above my head and I admit my knuckle-dragging self only got halfway through before switching to Marc Maron interview Wolfgang Van Halen but this one section caught my ear before giving up:

One of the big areas of improvement in the near future is inference time compute, applying more compute at inference time. I guess the way I like to describe it is that even a giant language model, even if you’re doing a trillion operations per token, which is more than most people are doing these days, operations cost something like 10 to the negative $18. And so you’re getting a million tokens to the dollar.

I mean compare that to a relatively cheap pastime: you go out and buy a paper book and read it, you’re paying 10,000 tokens to the dollar. Talking to a language model is like 100 times cheaper than reading a paperback. So there is a huge amount of headroom there to say, okay, if we can make this thing more expensive but smarter, because we’re 100x cheaper than reading a paperback, we’re 10,000 times cheaper than talking to a customer support agent, or a million times or more cheaper than hiring a software engineer or talking to your doctor or lawyer. Can we add computation and make it smarter?

This entire way of reducing signal to tokens and computation made me think of investment alpha. It made me think of how financial innovation*, the cycle of hunting for alpha, alpha decay, and efficiency works.

Professional investment managers with teams of salepeople pitch their funds “alpha”. They used to just say “look, how much money we made” but now they have to adjust for beta or some other benchmark. Allocators get smarter. The process is uneven but the waterline of basic aptitude does inch higher. If the market is mostly free of captive frictions then the need for return and the quest to provide it finds a clearing price.

But what does that equilibrium look like in the future? Well, probably something like the way it looks now regardless of how efficient it gets. The paradox of provable alpha is a stable attractor whereby the average person in pursuit of excess returns gets a random number distributed around a fair return so long as they avoid outright stupidity (like investing in levered ETFs for the long haul).

An efficient market feels random. Not to throw another paradox out there but this is exactly what Mauboussin refers to in “paradox of skill”. When the competition is evenly matched, luck determines the outcome. The funds and their marketers who survive all tout information ratios and charts which suggest their alpha, net of fees, is persistent. The best we can probably say about them is they might be good enough such that the claim is a coin flip. If they were deterministically better than a coin flip, they’d be inaccessible or would charge enough to skim the surplus.

But it’s getting into the realm of a coin flip that is the answer to job security. If you’re good enough to have your results look random it comes down to story-telling and dinner. Your value here might not be in delivering true alpha, but if you find a buyer you have created value — by definition you have given someone what they want.

[There’s a piercing conversation to be had here about commerce in general. If I sell snake oil or astrology is my income compensation for creating value? GDP and capitalism say yes. Is profiting from misinformation value-creation? How far does this go? The conversation gets quite “nudgy” if you focus too much on “what’s efficient” vs what tradeoffs are we willing to tolerate and for what ends. There’s a continuum.

Disagreement about object-level policy is downstream of differences in where people lie on the philosophical continuum. Nobody says “you should be allowed to pollute for a profit” but should you be allowed if that’s what people want? You’d want a polluter, the one with the upside to bear the risk, but I doubt even that anodyne statement is universally acknowledged. I could just as easily imagine an uber-industrial view that the people asking for the product should be forced to live with the pollution. Feel free to use pollution as a metaphor for FUD, artificially constrained university admission, or whatever profitable hobby horse irks you.]

If capital-compute-fueled efficiency makes it harder to create alpha or more generally “value”, it still won’t take away the types of value that are not provable. Maybe the only jobs remaining will be selling figurative placebos.

Now are they gonna pay enough to cover junior’s riding lessons?

Fck if I know. Ask a robot.

I know I’ll still be listening to Van Halen like the peasant I am. There’s probably something to that.


[Expanding on the asterisk from above]

*Financialization is an innovation because slicing up risks to sell to their highest bidder increases liquidity. An liquidity is a “good”. Liquidity reduces the cost of capital for industry. You will finance more businesses if you believe you can sell your shares. Insurance and mortgages are concrete products of the abstraction known as “liquidity”. All of this liquidity is an instance of abstractions that sit even higher in the stack — specialization, comparative advantage, and the surplus we enjoy from trading, I mean “trading” in the positive sum cooperative sense, with each other.

This harkens back to the liquidity premium discussion in Why Investing Feels Like Astrology:

Liquidity Premium

@Jesse_Livermore’s work refers to an idea he calls “transactional value”. It is the value that permits you to pay more than intrinsic value for an asset because you know you could sell it back into a liquid market.

Here’s Jesse parsing intrinsic value from transactional value:

The intrinsic value of equities would be the cash flow stream of the equities themselves, which you can collect and they belong to you and you can spend them and do whatever you want with them.

The transactional value would be the value that comes from the fact that there’s this “network of confidence” in the market, that people have been doing this for hundreds of years and we know that when you wake up tomorrow, the S&P is not going to be at 500. It’s going to be near where it was yesterday and people are kind of anchored to where its price is…You can basically take all your money, 100% of it, and put it into the stock market and know that you’ll be able to get a lot of that out anytime you need to. That’s the transactional value, which is the premium.

The idea that liquidity commands a premium is not new. If you have any money in a savings account today, you are paying a liquidity premium in the form of negative real interest rates. The treasury market discounts off-the-run securities because they are thinly traded even though they mature to the same value as their on-the-run counterparts. But I don’t want to dismiss Jesse’s notion of transactional value because it’s not novel. His expression of it is illuminating. For example, currency is made entirely of transactional value. The fact that we can rely on it to trade warrants a premium entirely out of proportion to the value of paper that represents it.

Seasonal volatility

On Jan 28th, one of my favorite topics came up in the Moontower Discord: natural gas options!

I was asked why the VRP was so low.

Recall VRP is the comparison of implied vol (forward looking) to realized vol (backwards) looking. In this datapoint,

One month IV = 49%

One month RV = 86%

The strange datapoint is a perfect icebreaker for discussing:

  • seasonality (which happens to be most strongly expressed in natural gas)
  • a common pitfall (and potential correction) for VRPs

     

Background

Before discussing options, we need to understand the shape of seasonality and the fundamentals that drive it. I’ve said many times that I’m not a fundamental trader. That means I don’t position based on any views about fundamentals. But a basic understanding of fundamentals is necessary to make sense of why an asset’s vol surface looks the way it does.

Let’s begin…

 

A Brief Primer on Natural Gas Dynamics

Natural gas prices follow a seasonal cycle, with volatility peaking in winter due to heating demand and spiking again in summer due to electricity consumption.

Seasonality volatility

Winter is the most volatile season.

  • Heating demand: Cold weather drives demand
  • Supply constraints: Limited storage or pipeline capacity can trigger price shocks.
  • Weather uncertainty: Forecast swings can cause sharp market reactions.

Summer is the next most volatile season.

  • Electricity demand: Power plants burn more gas for cooling
  • Hurricane season effect on supply: Storms in the Gulf can disrupt production

The Storage Cycle

  • Injection Season (April–October): Gas is stored for winter, with October marking peak supply. If storage maxes out, prices can collapse.

    [In 2009, this was a major risk with the Oct $2.00 put price surging to an insane vols on extremely heavy volume. I remember feeling terrible for leaving my business partner to deal with that expiration on his own because I had to be in Mexico for my wedding week. He was able to join the festivities after making sure we weren’t going to need a cave to take delivery. I distinctly remember computing that the stretched IVs still never reached the extreme levels of realized vol that accompanied that expiry. On a hedged basis, every option except the ones where Oct gas expired were a buy. The market found the path of maximum pain.]

    Injection season is often traded as a package of futures of options known as the “J-V strip” based on their futures month codes. In trader language, the “ape-oct strip”.

  • Withdrawal Season (November–March): Stored gas is used to meet demand, with March marking peak depletion—low storage levels can drive price spikes.

    This season is also traded as a package — the “X-H strip” or “Nov-March”

…which brings us to the “widowmaker”.

 

March-April Spread: A Market Tightness Gauge

The March-April futures spread more affectionally known as the “widowmaker” or simply “H/J”:

  • High March premium: Indicates low supply and potential scarcity.
  • Weak or negative spread: Suggests ample gas and lower risk.

I’ve written at length about this spread and the options on it.

🔗What The Widowmaker Can Teach Us About Trade Prospecting And Fool’s Gold

You can learn a lot from its vol surface that can be applied to any asset with a “bubble” distribution. Moontower’s ever-so scientific definition: a price that most likely collapses but can reach any arbitrarily high price before it tanks.

🔗What Equity Option Traders Can Learn From Commodity Options

 

Supporting evidence in pictures

 

Exhibit A: Natural Gas Inventory 5-Year Seasonality Chart

Exhibit B: A historical snapshot of the gas futures term structure

Exhibit C: Realized vol by month

moontower

Exhibit D: Despite the strong realized vol seasonality the range of volatilities both across and within years is itself quite volatile.

Exhibit E: The March/April futures spread

The “widowmaker” expires this month. In commodity land, futures spread are usually quoted as near month – back month. So in a backwardated market the spread would be positive (ie March > April).

In equity markets the convention is reversed. The price is quoted as back month – front month. The charts below are from IB which uses equity market convention.

You can see the “winter premium” come out of the spread as April is now trading close to parity with March but the spread was negative (ie April < March for the past several months).

This is typical behavior. The spread usually goes to parity as the fear of a cold winter subsides. But it’s dangerous to short early in the season because the spread can go extremely negative (if you’re looking at the price using the IB quoting convention…which burns my eyes but whatever).

H/J 2025 future spread

Here you can see the spread for 2026. April is trading at about a 32 cent discount to /March (~10%). If next winter is mild, you’d expect the gap to close.

H/J 2026 future spread

In the below charts we respect tradition by using the quoting convention of March – April…you can see the destination of the spread is usually ~ 0:

This was the spread in 2007 when John Arnold became a legend stuffing Amaranth’s Brian Hunter’s attempt to squeeze H/J:

 

Option surface dynamics

Let’s see how these fundamentals influence the vol surface.

Skew Feature

🔀Inverted skew

Call IVs typically trade at premiums, often steep premiums to puts. Because gas is prone to squeezes it often maintains a “spot up, vol up” dynamic. On the downside, gas can find incremental demand via “coal-switching” whereby gas prices become competitive with coal as a input to electricity generation. This source of demand dampens vol as futures fall reducing the probability of a complete collapse in an oversupplied market.

This is a chart of Feb gas options (note that Feb options expire in January…in commodities the contracts are named after their delivery month not their expiry month). The curves represent roughly 2 weeks and 3 months to expiry. You can see the skew inversion.

💡Learning moment: Note how skew looks steepens when DTE is smaller. Much of this is an artifact of the X-axis being in strike space not delta delta space. Why does that matter? Because how “far” a strike is depends on time. If gas is $3.00, then the $3.20 strike is much further (ie lower delta) with 2 weeks to go than 3 months to go. Low delta options usually command premium IVs.

 

Term Structure Feature

📅Seasonality in the forward vols

We know that realized vols are higher in the Winter. Look at the vol term structure I pulled from the futures options via CME.

2 things to note:

  1. LNF6 and LNG6 slope upwards indicating a higher volatility than Q42025 vols. This makes sense those 2026 capture December and January coldness while LNZ5 December options only capture through Thanksgiving. This tracks, nothing weird.
  2. Those winter vols implied vols are LOWER than Spring 2025 vols (ie LNK5 or May). What the heck?!

You have 2 forces colliding from opposite directions.

a. We absolutely expect vol to be higher next winter than this spring

b. Deferred futures contracts don’t move as much as prompt ones.

In other words, the beta of those winter contracts to whats happening now is low. Today’s supply/demand balance for gas has only modest impact on future prices. This is actually a universal effect in commodity futures. This is easy to deomonstrate if we consider a long duration between contract months.

The price of oil today has little impact on what the 5-year future does. Which makes sense. Near term drivers of oil could be weather, refinery outages, shipping logistics, and the current economy. Longer term, oil prices depend on drilling projects, regulations, and the state of economy which is anyone’s guess from our current seat. A price spike today, can lead to more investment in oil, which would increase supply in the future. Nobody thinks that a near term squeeze should have an equal response in the deferred month.

The quantitive observation that deferred months have lower realized than near months is called the Samuelson effect. Stated otherwise, contracts become more volatile as expiry approaches

💡This is a strong effect as a contract travels from being a 12 month contract to a 1 month contract but effect is smaller as a contract goes from being 10-years to 9-year or from 20 days to 1 day. The schedule of how variance decreases as DTE increases looks like a curve. Hold this thought.

The stronger the Samuelson effect, the more downward sloping you’d expect the term structure. The fact that the deferred months are only slightly lower vol and the curve is flat actually implies an ascending term structure if you adjusted for Samuelson effect.

The schedule of how Samuelson unfolds has a tremendous impact on what you believe the term structure actually says. If there was zero Samuelson effect, then the term structure you see is the actual term structure which you are then free to extract forward vols from. That’s the case of equities where all the options are struck on the same underlying as opposed to each expiry referencing a different deferred future.

The stronger the Samuelson effect, the more true term structure and forward vols ascend. If your 1 year future trades at the same implied vol as your 1 month future despite the fact that the 1 year future is moving less, means that the market is implying more variance in the coming months. If there was no Samuelson effect than you’d assume a flat forward vol not an ascending one.

Armed with this knowledge, I present the UNG vols.

The bottom panel shows UNG vols ascending thru 2025, not descending like the futures options were.

UNG options are struck on a single underlying just like regular equity options, but that underlying ETF maintains exposure to the front month natural gas futures.

In the futures options, the January expiry references a deferred future and expires in December. It is an option that references a contract that will not be moving very much for the next few months, but will be whipping around like crazy near the end of its life.

The January UNG option is referencing a prompt future that moves around a lot and will converge to the futures option in the month of December when the ETF is holding the same contract January futures option references.

The key to translating the futures options vol into a UNG equivalent vol is a schedule for the Samuelson effect. This creates a model that allows market makers to relative value trade the futures options vols vs the ETF vols. (This was central to my strategy which required normalizing commodity vols into something that can be coherently compared to other vol surfaces).

Some food for thought:

✔️Instead of designating a Samuelson schedule, you can invert the problem. What Samuelson schedule needs to be true to make futures options and UNG options be relatively in-line?

✔️How does that schedule compared to how vol unfolded in prior years?

✔️In what ways is the fundamental context of this year different from prior years?

I’ll close this section with one more picture.

That is the forward vol matrix from UNG courtesy of moontower.ai on 2/4/2025

Recall this chart:

Winter vols average in the low 50s. The forward implied vols are pricing upper 50s. That is a normal premium and if you track the forward vols every day you’ll notice that winter vols 6-12 months out will price somewhere between mid 50s to mid 60s in the case that the upcoming winter supplies look tight.

💡Winter volatility is right-skewed so if the realized avergaes low 50s the median can be assumed to be lower but sometimes the vol is much higher than the 50s. You can see the “polar vortex” in Feb 2014. You can also see just how low the vol can be in the winter:

That chart shows how deferred forward vols are like fair point spreads but have giant error bars compared to the range of realized outcomes.

 

Additional thoughts

✔️Circling back to the question that launched the post: why was the VRP (ratio of IV to realized vol) so low on January 28th?

Like looking at VRPs after earnings it’s an instance of a VRP failure mode — you are comparing a forward-looking numerator to a backwards-looking denominator. As we change seasons, nobody expects the recent bout of volatility to repeat in the next month.

✔️An example of a trade I did in the mid 2010s

I don’t remeber the exact year but in the early spring, summer vols were getting smashed as producers were selling calls as part of large hedge programs, They were bombing summer call strips. For example, if they sell 5,000 J-V $5 calls they are selling 5,000 calls in each of April, May, June, July, Sep, Oct.

30k call options in total.

I don’t remember how many total calls were sold or how long the program lasted but at some point the vols looked quite tasty.

I eyed July 4 calls which a broker was offering for 10 ticks. 10 ticks = 1 penny. So to breakeven gas had to go to $4.01

A natural gas tick is worth $10 so each option cost $100. I bought 10k for $1mm of premium. Gas was trading in the low $3 range at the time. I decided the best way to manage the trade was to risk budget it instead of delta hedge it. The options were a very cheap vol but I didn’t want to invite the path risk of selling deltas on a grinding rally where a summer risk premium started to emerge if it was looking like a hot season. Instead, I would play for a spikier move. I remember pulling up some historical charts and figuring based on an admittedly low sample size that the chance was somewhere around 20% but if it happened I’d conservatively make 9-1 on the calls. I also asked some sell-siders about whether there was anything in the fundamental context that differentiated this year from prior years.

[There’s a concept I call “analog” years where some years look like others. “In 2007 corn plantings were at this stage by this time of year and everyone thought that summer was going to be hot and the vol surface liked like this”, etc.

I didn’t check on these things so much to ideate a trade as to just check if I was missing something baked into the common knowledge the underlying market when I’m reacting to a trade.]

All told, it was reasonable to risk $1mm in premium, all-or-nothing.

So did the calls hit?

No. But, I was right about the vols being low. It was still early spring and the futures weren’t going anywhere, but the calls stayed penny bid for the next month. A month elapses, spot goes nowhere which means the IV on the strike clearly increased.

From there I had choices, I could re-asses if I thought the vol was still cheap. If not I could roll the calls up, or sell some closer-to-ATM vols and still be long vol-of-vol. If I thought the vol was still seasonally cheap, I could roll them down and have more gamma as the futures started to roll up the Samuelson curve (ie move around more). The point is there was a new set of decisions but they have nothing to do with the original trade which was “buy the cheap vol, decide how to manage it”.

In the end I was right but didn’t make a sum of money that stands out in my memory. This is not especially unusual. Trading be like that.

Extensions to think about

✔️Earnings seasonality

Market-maker’s starting point for thinking about earnings straddles will be:

  1. How much has the stock moved on prior earnings dates
  2. How was the earnings straddle priced going into those dates

I expect they also consider earnings seasonality. If a retailer makes most of its money in Q4 then the process for pricing earnings won’t be uniform every quarter. The sample size of relevant earnings history will be even smaller as each year maybe there’s only 1 day that is a true analog for appreciating how many days of volatility should be baked into the earnings straddle.

I’d totally expect that the market handles this well. I’m just relating the idea of seasonal volatility to assets outside commodities.

✔️Ags and softs

It’s not surprising that I took the nat gas framework and pointed it at cotton, cocoa, sugar, coffee, soybeans, corn, and wheat. Each of these markets has its own idiosyncrasies. Examples:

  • peculiar option to future expiry mapping
  • seasonality drivers
  • concepts like “old crop” vs “new crop” which means Samuelson curves are discontinuous
  • import/export features => currency correlation considerations
  • unique natural flows

As a vol trader you are doing some mix of modeling and qualitative adjustments to estimate the implied forward vols in these markets.

💡It’s critical to understand how the distribution of variables that roll up to those numbers effect how the forward vol estimates are distributed…the weaker you think the Samuelson effect is the more you will be inclined to buy time spreads. Are you buying time spreads while your modeling of Samuelson is on the low end of its range? Then realize that your position is more vulnerable to near term stress than your headline greeks would suggest.

If you use percentiles to measure skew, vol or any other metric are you conditioning them on season?

Would it make sense to condition on the degree of backwardation or contango in the market?

Ok, I’m going to leave it there.


If you are interested in commodity vol stuff either directly or just to expand your own option-thinking toolbox check out:

the right bogey: trades that seem compelling but aren’t and vice versa

In value over replacement, I explained a handy feature of option theory or really derivative pricing broadly is it models important aspects of decision-making explicitly. Especially opportunity costs:

In options, the opportunity cost can be thought of as the risk-free rate. But the risk-free rate is an instance of a category we call benchmark.

Professional investors separate alpha from beta by benchmarking to an index. We can get fancier into benchmarking by using factors. Private investments can be subject to hurdles. All of these ideas are focused on the same question:

What is the marginal contribution of an action or intervention?

This is important because that’s what we compare the marginal cost to.

I discuss later in the post that structured products appear to have a compelling pitch by a sleight of hand. They prey on our “VOR blindness” when they announce that they can’t lose money. It’s a sales tactic that ignore opportunity cost. If I return 1% in a world with a 5% risk-free-rate or even 3% inflation I’m just falling for a real vs nominal illusion. My capital has lost ground despite the 1% gain.

[If you would buy these structured notes but be unwilling to spend your bond coupons on index calls you either don’t understand that you are doing the same thing in principle or you are saying I’d rather pay someone to do this. Either is ok to admit, just have your eyes open.]

In that example, making opportunity costs explicit neuters an otherwise compelling pitch. But this can also work in reverse. We can make an uncompelling pitch favorable.

I’ll give 2 examples from the trading world.

✔️Zero or negative edge trading strategies

You’re running a large delta-neutral vol book. It spits off tons of deltas as stocks move around and gamma varies. You need to continuously hedge. Assume your explicit and implicit (ie slippage) hedging costs are 10 bps.

Imagine you came up with a mean reversion stat arb strategy that had zero pre-transaction cost expectancy. Hell, pretend the strategy has -5 bps of expectancy.

Instead of facing the “street” on all these delta hedges you could internalize them by allocating them to the stat arb book. The book is nominally delta-neutral but might lose less in expectancy over some assumed holding period than constantly turning your deltas over on the exchanges.

In other words, a strategy that would be a non-starter from an alpha POV is worth doing because it loses less than the alternative. The bogey is not “we need to make positive edge” but the explicit cost of otherwise paying 10 bps.

By properly benchmarking our decisions, we have turned an uncompelling pitch to a favorable one.

[Real-life observation: Index Trader A is short QQQ gamma and Trader B is long AAPL gamma going into earnings and the stock has a big move down. Trader B needs to buy AAPL and Index Trader B needs to sell it. AAPL is 9% of QQQ so if the index book is 11x bigger than the single stock book and they have matched greeks, then the buy and sell orders would happen to pair off. But even if they didn’t the deltas between the 2 books would be virtually paired off and the firm would hedge the residual in the open market. This saves transaction costs and slippage on gross position sizes.]

✔️Option “dissection”

In the clip below (excerpted from the large screencast), I explain how market makers use synthetic and arbitrage structures like condors and butterflies to “chunk” risk by themes. They can then remove such well-defined strategies from their main risk view so they don’t have to hedge the greeks they spit off.

It’s not alchemy as far as edge. It’s simply splitting your risk into those that can be safely cordoned off vs ones that need more management (open ended exposures to vol or higher moments of the distribution).

In a large options book you have all this open interest because you got paid to buy or sell it at one point. But now it’s just stale inventory. You have no view on it. It’s effectively random risk. But it’s expensive to flatten it all.

[Actually it’s incoherent to do so. The whole reason you have a business is because someone needs to warehouse the risk that arises due to a mismatch in timing and desire — hedge fund A wants to buy puts on Tuesday and mutual fund B wants to sell calls on Thursday. Your role is to trade with both of them and manage the vertical spread they’ve effectively foisted on you. Sequentially to boot. You were forced to be short vol for 2 days in the interim.]

Your risk management logic looks like:

a) I need to hedge

b) Hedging is expensive

c) Can I reduce hedging costs proportionally more than the risk of being less hedged adds?

In other words, your risk management criterion is against an inevitable cost. The hedge is not positive expectancy, it just needs to reduce risk at reasonable cost or reduce costs without adding risk.

Dissection reduces costs without adding risk (although it changes the shape of risk. If you are indifferent to the new shape it gives you choices and those choices need not have anything to do with being profitable — they just need to lose less.)