F-innovation

I went on Resolve Riffs with Adam Butler and Rodrigo. It was a totally free-form no prep episode. We mostly talked education and parenting stuff. There’s investing repartee on the back end.

 

It’s worth an evergreen reminder — The InvestResolve team did a great podcast series teaching risk-parity which is another term for diversified portfolio (it’s just that the term “risk-parity” implies the weightings depend on the volatility and cross-correlations of the portfolio components).

I published a summary a few years ago:

InvestResolve Masterclass On Risk Parity (Moontower guide)

If you are short on time focus on the first 3 parts:

In addition to his work at InvestResolve, Rodrigo collaborates with Corey Hoffstein to lead the Return-Stacked ETF push which is a way to maximize the benefit of diversification, namely maximizing return per unit of risk, via capital efficient leverage.

I think one of the coolest aspects of these products and the education around them is what it says about the waterline of investing knowledge — it’s constantly rising. What the institutional world understands about portfolio construction trickles down to retail on a lag but it does trickle down.

The lag depends on a mix of:

  • regulation (ie portfolio margining)
  • complexity (advisors are the messengers of new financial innovation to most of the public although there’s plenty of asset manager blogs or even blogs like this one that reach DIY investors)
  • cost (fintech can scale the some of the analytical, data, execution, and funding over large user bases)

The Return Stacked funds bring the same techniques for structuring efficient portfolios that professional fund mangers have understood for decades to retail investors.

Corey does an amazing job explaining the principles in this video interview in a simple way:

🎙️Building a 100% Stock Portfolio Using Return Stacking (Millennial Investing)

My notes:

Rethinking How Your Portfolio is Constructed

Modern Portfolio Theory tells us to find the most diversified portfolio and lever it up. AQR’s Cliff Asness showed that if you take a portfolio that looks very close to a 60-40 and lever it up 1.5 times, historically, you would’ve had a higher return and about the exact same risk as equities. They call diversification “the only free lunch in markets”. It largely is. There’s no benefit really to foregoing diversification, but often you have to use leverage to really unlock those benefits.

Most people in 100% equities know that when you go to a 60-40, you’re de-risking your portfolio — you’re selling stocks to buy bonds that are less risky. The only way a 60-40 can compete, even though it’s more diversified, over the long run is by levering it back up to the same amount of risk.

  • Notes on tax efficiency
  • Leverage
    • optimal math number vs behaviorally prudent number (difference bt risk capacity and risk tolerance)
    • Leverage has bad reputation but if only if you pair it with concentration. All disasters have leverage at the scene of the crime but usually to increase a concentrated position.
    • leverage + true diversification is an unlock and really the big thing that institutional investors understand that the average investor doesn’t. That’s the key innovation here — capital-efficient exposure to leverage while diversification keeps the risk unchanged
  • Fees are lower than they appear because need to normalize them to amount of risk

Finally in the spirit of retail investing strategies getting smarter, the post I wrote on Thursday is on the topic you are going to hear a lot more about using your existing portfolio to collateralize a long/short overlay enabling the possibility of generating additional alpha as well a bank of short-term tax losses which can be applied in the future to match the timing of selling your large winners.

“Alexa, quiz me on photosynthesis”

Friends,

A bunch of quick observations and recs today especially around investing.

I went on Resolve Riffs with Adam Butler and Rodrigo. It was a totally free-form no prep episode. We mostly talked education and parenting stuff. There’s investing repartee on the back end.

A cool thing Rodrigo taught me was how he told Alexa “Enable ChatGPT”.

Then at breakfast you can prompt it with “Hey ChatGPT you are tutoring my 6th grader in Spanish (or her photosynthesis or whatever), quiz her”.

The kids are going back-and-forth over breakfast vocally with ChatGPT and their grades show it!

I started doing this with boys the next day. Zak’s Egypt test in social studies was Friday. We used the ChatGPT app to converse with the bot using the phone mic and speaker. We uploaded screenshots of the materials and it quizzed him. We even had to tell it to keep the questions focused on what was in the materials because it tried to quiz him on more Egypt facts than the test covers.

We got a bonus benefit too. It was a rainy day and Zak wanted to practice hoops in the garage so he asked ChatGPT to give him a dribbling and calisthenic workout to follow. I didn’t even know until he came back inside and I asked where he was. Good initiative bruh.

If interested, I talk about Math Academy in the interview as well. I also gave a talk to my local social club about it Wednesday night. The boys (and I) are still going strong with it and I don’t even tell them to do it. At least once a week they are logging XP before I wake up. If you’re looking for math enrichment for you, a kid, grandkid, student give it a peek.

 


Money Angle

I tweaked the Cockpit to highlight the change in markets since the close of Friday before the election. A lot of the gains were clipped a a bit this week.

A few things that popped out:

  • Equity indices are up .5 to .9 standard deviations. In pure percent terms, IWM is the biggest winner (4.2%) and QQQ the laggard (1.9%)
  • International stocks are down about .8 standard deviations…which ties into the next point…
  • USD is up, yields are up slightly and gold is down 2 standard deviations or 6.5%
  • Meanwhile BTC is the mirror image…up about 2.5 standard deviations or nearly 28%!
  • There’s dispersion under the hood of equity indices with winning and losing sectors:
    • XLE (energy), XLF (financials), XLY (consumer discretionary), XLI (industrials) are all up between 1 and 2 standard deviations
    • Biotech and healthcare are down over 1 standard deviation (XBI is down almost 8%)
  • Finally just looking at a few mega stocks:
    • TSLA is up 2.7 standard deviations or 25%!
    • NVDA is up .65 st dev or 4.7% while TSM is down .55 st devs or 3.7%
  • Finally VIX is down from about 22 to 16 (and that includes a greater than 1 point rally on Friday)

💡A note on standard deviation:

I’m dividing the move sizes annualized, by the implied vol of a 2 week option on Friday November 1st.

This cockpit view is coming to moontower.ai this month. Our devs showed me the prototype this week.


I don’t know anything about the future so I follow a permanent portfolio/all-weather/cockroach type investing strategy. The focus is on diversification which is subscribing to a strategy that means always having to say you’re sorry.

Fyi YTD returns for a few major assets:

SPY and gold ~+23%

BTC ~ +115%

TLT (long term treasuries) ~ -4%

US dollar index ~ +5%

Eurostoxx ~ +8%

The InvestResolve team did a great podcast series teaching risk-parity which is another term for diversified portfolio (it’s just that the term “risk-parity” implies the weightings depend on the volatility and cross-correlations of the portfolio components).

I published a summary a few years ago:

InvestResolve Masterclass On Risk Parity (Moontower guide)

If you are short on time focus on the first 3 parts:


Rodrigo and Corey Hoffstein lead the Return-Stacked ETF push which is a way to maximize the benefit of diversification, namely maximizing return per unit of risk, via capital efficient leverage.

I think one of the coolest aspects of these products and the education around them is what it says about the waterline of investing knowledge — it’s constantly rising. What the institutional world understands about portfolio construction trickles down to retail on a lag but it does trickle down.

The lag depends on a mix of:

  • regulation (ie portfolio margining)
  • complexity (advisors are the messengers of new financial innovation to most of the public although there’s plenty of asset manager blogs or even blogs like this one that reach DIY investors)
  • cost (fintech can scale the some of the analytical, data, execution, and funding over large user bases)

The Return Stacked funds bring the same techniques for structuring efficient portfolios that professional fund mangers have understood for decades to retail investors.

Corey does an amazing job explaining the principles in this video interview in a simple way:

🎙️Building a 100% Stock Portfolio Using Return Stacking (Millennial Investing)

My notes:

Rethinking How Your Portfolio is Constructed

Modern Portfolio Theory tells us to find the most diversified portfolio and lever it up. AQR’s Cliff Asness showed that if you take a portfolio that looks very close to a 60-40 and lever it up 1.5 times, historically, you would’ve had a higher return and about the exact same risk as equities. They call diversification “the only free lunch in markets”. It largely is. There’s no benefit really to foregoing diversification, but often you have to use leverage to really unlock those benefits.

Most people in 100% equities know that when you go to a 60-40, you’re de-risking your portfolio — you’re selling stocks to buy bonds that are less risky. The only way a 60-40 can compete, even though it’s more diversified, over the long run is by levering it back up to the same amount of risk.

  • Notes on tax efficiency
  • Leverage
    • optimal math number vs behaviorally prudent number (difference bt risk capacity and risk tolerance)
    • Leverage has bad reputation but if only if you pair it with concentration. All disasters have leverage at the scene of the crime but usually to increase a concentrated position.
    • leverage + true diversification is an unlock and really the big thing that institutional investors understand that the average investor doesn’t. That’s the key innovation here — capital-efficient exposure to leverage while diversification keeps the risk unchanged
  • Fees are lower than they appear because need to normalize them to amount of risk

Finally in the spirit of retail investing strategies getting smarter, the post I wrote on Thursday is on the topic you are going to hear a lot more about using your existing portfolio to collateralize a long/short overlay enabling the possibility of generating additional alpha as well a bank of short-term tax losses which can be applied in the future to match the timing of selling your large winners.

 

Money Angle For Masochists

🎙️Strong Source Interviews Ed Turner (70 minutes)

In this episode, we welcome Ed Turner, an experienced commodity trader with over a decade in the energy markets. Ed discusses his journey from trading base metals at Mitsubishi UFJ to leading Mandara’s trading desk.

Now a Senior Trader at Gunvor and an entrepreneur with Shogun Sakes Ltd., he shares insights on navigating oil trading dynamics, the transition from large firms to smaller, high-intensity environments, and the importance of risk management. Ed also explores the psychological aspects of trading and his shift from market-making to a more strategic, balanced approach.

Ed ran Mandara’s trading desk. They are not commodity traders trading around physical assets. Like my own past oil trading life they trade “paper barrels.”. Ed alludes to the same idea I’ve harped on before when interviewing candidates from banks who are used to trading around client flow— when you come to the buyside all you have is capital. You get a computer and a phone. Make money come out of it. The interview articulates what that problem looks like better than I’ve been able to. It’s a poker game. And it’s a grind. From listening to Ed it also strikes me that Mandara is a prop trading firm that resembles a market maker — philosophically and in practice. Ed wrote the firm’s risk manual and was heavily involved in education in addition to running the desk. Strong recommend.

 

Stay Groovy

☮️


Moontower Weekly Recap

the option market’s point spread (part 2)

In part 1, the option market’s point spread, we introduced the idea of the VRP or volatility risk premium which sets the line on whether an option buyer or seller will win. Usually the sellers win but that statement is uselessly low res.

💡When we say “win” we mean even in expectancy terms. In frequency terms it’s even more true. From Straddles, Volatility, and Win Rates:

Expectancy and win rate are not the same. Remember that the most you can lose is 12% but since there is no upper bound on the stock, your win is theoretically infinite. So the expectancy of the straddle is balanced by the odds of it paying off. You should expect to lose more often than you win for your expectancy to be zero since your wins are larger than your losses.

So how often do you theoretically win?

A fairly priced straddle quoted as percent of spot costs 80% of the volatility. We know that a 1-standard deviation range encompasses about 68% of a distribution. How about a .8 standard deviation range?

Fire up excel. NORMDIST(.8,0,1,True) for a cumulative distribution function. You get 78.8% which means 21.2% of the time the SPX goes up more than .8 standard deviations. Double that because there are 2 tails and voila…you win about 42% of the time.

So in Black-Scholes world, if you buy a straddle for correctly priced vol your expectancy is zero, but you expect to lose 58% of the time!

My teaser for this week’s post claimed:

[This week] we will go a 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.

The VRP computation (IV/RV) is just one measure of relative value. There’s no single point spread.

It’s easy to demonstrate this by casting doubt on the denominator. Here’s a thought exercise:

Stock ABC has a VRP of 10%.

Its IV is 17.6%

Its realized vol based on the last 20 days of daily log returns is 16%

📅16% annual vol is approx 1% per day…16%/sqrt(251)

17.6/16 = 1.10 – 1 = 10% VRP

…but

Now I tell you that the stock went up every single day by 1%.

💡If you compute the standard deviation the standard way by subtracting the sample mean (ie x̄) you’ll actually get a standard deviation of zero. If an asset has exhibited a steady trend this is obviously misleading since calling a stock that went up 1% per day for 20 days “zero vol” drains all semantic meaning from “vol”. The fix is easy…when you compute realized vol just don’t subtract the mean or use mean = 0 before squaring the individual returns. This caveat wasn’t the point of this exercise but if your antennae went up, fair play to you.

What’s the volatility of this stock?

Sampling daily returns we get 16%. But the stock is up 22% in 20 days.

We can annualize that point-to-point return:

22% * sqrt(251/20) ~ 78% realized vol

We can annualize the weekly (ie every 5 day returns):

5% * sqrt(251/5) ~ 35.4% realized vol

You get the picture.

What is the right vol for the option?!

16% seems way too cheap given what just happened.

So depending on what vol you pick your VRP ranges from 10% on the high end to 17.6/78 – 1 = -77% on the low end.

There’s not one point spread!

Realized vol is sensitive to your sampling periods. And I’m not even getting into super-fast updating vols (computing realized vols from tick data, a fun rabbit hole of its own).


On the desk, I was always on alert for highly divergent vol readings based on sampling periods.

[This is hardly a silver bullet. The implied vol on the hypothetical stock above is likely to be higher than 16%. The market’s not stupid.]

Honestly, I didn’t screen for those scenarios explicitly. I traded commodity options. The universe was relatively small so whenever I looked at realized vol numbers, which I did often, I had a feel for whether they made sense. If the realized vol (sampled daily) in gold is 12% but the metal is up 7% in 2 weeks I know the realized vol is misleading.

7% * √(52/2) ~ 36%

That’s like a 36-vol move. If near-dated options are trading at a 10% or even 20% VRP to 12% realized (or 13.2% to 14.4%) I’m out there accumulating a long gamma position.

I didn’t have a tool to necessarily flag these scenarios but if you trade a relatively short list of names all the time you build a mental history. I’d know which brokers were selling vol in the name, I might ask them where their customers are offering, or I might even go to brokers who were buying at cheaper vol levels before the move and see if they want to sell at the higher IVs and “take profits”.

[The game is a mix of what the cards are (examples include implied and realized vols) and human behavior —who has an axe to buy or sell and how do those axes change with the cards.]

The point is there’s a bunch of tacit knowledge that I don’t bother displaying on yet another monitor.

[There’s a wiseguys-trying-to-outdo-wiseguys snark about having lots of monitors. Like real Gs need nothing more than a laptop. You know something, being Warren Buffet or a VC is nice work if you can get it…but if you get the chance to visit the office of a market-making group you’re gonna see a LOT of screens. My set-up had 6 24s, a tablet for Cloud9, and windows into several virtual machines. What do you want me to say…professional trading is a video game. Put a price on 100k vega in comp, you have about as much time as it takes to move your eyes while chatting them up about last night’s World Series game.

I can see how a normal business person might think this is crazy. Lucky for them, most jobs are civilized. If you want to look down on the animals who need a wall of monitors you’re only soothing yourself — the feral don’t give a f what tool you use to convert time to cash.]

Using the data and background on VRP in last week’s post we can examine my tacit hunches more closely.

The goal of the post is to:

  1. inspire seasoned traders to explore fresh inputs into pricing volatility
  2. for novice traders, to have each of the building blocks in the exposition expand their frontier of knowledge a little further.

Ratio of realized vols sampled at different frequencies

In Risk Depends On The Resolution, we see that volatility depends on the sampling frequency. In general, more frequent sampling results in higher levels of measured volatility. This is a relevant observation for all investors not just option traders. It means that simply looking at an asset’s annual or even monthly returns smooths (if you are a long-term investor) or masks (if you run a strategy whose stakeholders are shorter-term oriented) the path. It’s a warm blanket for the patient and dragon for the churner. Whether the observation is reassuring or a warning depends on the context.

(I leave it to the reader to spot the asset management marketing departments who use this observation to flatter themselves by invoking it inappropriately).

For our purposes today we will measure 1-month realized volatility at 2 sampling frequencies:

  • daily (day-over-day logreturns)
  • weekly (5-day point-to-point logreturns)

Our monthly window will constitute 20 business days, therefore 1-month vol sampled:

daily means 20 returns or data points

weekly means 4 returns or data points

🗓️As a reminder we are using data from the past year (10/11/23 to 10/16/24).

 

Across our 43 names, the average ratio of volatility sampled weekly vs volatility sampled daily is 94%.

By example, that means a stock that realized 10% volatility using daily returns for the past month, would have realized 9.4% volatility if we sampled weekly instead.

Only 5 names had a realized vol that was higher when sampled weekly instead of daily.

This is in keeping with the general empirical principle — volatility sampled less frequently tends to be lower.

However, there is tremendous variation in this ratio even if it averaged 94% over the full sample. The standard deviation of the ratio is a whopping 35% meaning 2/3 of the time the ratio was between:

  • 59% — the daily sampled vol was 66% higher the weekly sampled vol!
  • 129% — the weekly sampled vol was 29% higher than the daily sampled vol.

The lower measured vol effect from less frequent sampling holds generally, but it’s very noisy.

A word on trending vs mean-reversion

Going back to our introductory puzzle, if a stock goes up 1% per day for a month its vol, if we sample weekly, is much larger than if we simply annualize that typical daily volatility.

The ratio of vol sampled weekly / vol sampled daily is much greater 100%. This scenario corresponds to our colloquial understanding of the word “trend”. The stock “trended” higher. A quant might say the drift dominated the volatility. As far as I know, this ratio being > 1 is not an accepted definition of “trend”. But even if it is not formally defining, I suspect it’s a common characteristic of a market that is labeled “trending”. (I have a post in the queue that will unpack this further so we will put a pin it in for now.)

Regardless of how the wider quant community views trend, the ratio and its suggestion of trend is deeply relevant to option traders.

If the ratio is greater than 1, the long option holder will have wished “they let their gamma run” while the short option trader will have wished to hedge more frequently.

I suspect any option trader reading this will drink to that since the memory of how they hedged is inseparable from large p/l events, positive or negative.


Ya know what, let’s take a breath and acknowledge something…”ratio of realized vols sampled at different frequencies” is a miserable mouthful. Just take a moment to digest it. It refers to the same window of time, it’s just that the numerator (weekly sampling) is less frequent.

Another way to think of it: it takes longer to converge to a estimate of the volatility

If we computed volatility based on 10-year returns you’d die before you felt like you had a reasonable guess of the asset’s volatility. A long sampling period is a slow-moving measure of variation. Higher frequency sampling gets us to a reliable measure of volatility much faster.

While we’re at it, I have another simplification.

Sacrificing formality for ease of readability, let’s call the “ratio of realized vols sampled at different frequencies” the trend ratio. If the weekly sampled vol exceeds the daily sampled vol we are trending, if it’s lower there’s mean-reversion. (Again, not officially, and don’t tell the quant police or the publishers over at Wiley.)

From trend ratio to VRP

We typically measure VRP as the ratio of implied vol to realized vol sampled daily. But there’s no single VRP. We could make the denominator realized vol sampled weekly or any other interval.

Let’s consider a VRP using the weekly sampled vol.

If the weekly sampled vol is greater than the daily sampled vol (a trend ratio greater than 1), the VRP is algebraically pulled lower. Options appear cheaper.

We expect the options market to correct for this when the trend ratio is much greater than 1 by bidding the implied vol higher.

We expect that a trend ratio greater than 100% will coincide with elevated VRPs when the VRP is computed traditionally (ie with a daily sampled realized vol denominator).

Just looking at the bulk data across names (we limit the x-axis to 2 standard deviations on either side of mean of .94), there’s no relationship.

Let’s look by name.

This is a table of VRPs partitioned by trend ratio. The names that are mostly green have low VRPs and the red ones have had lots of volatility risk premium.

My hunch was that high trend ratios (where weekly sampled vol is much higher than daily sampled vol) would correspond to higher VRPs as the market understands that the traditional measure of realized vol is understating the variance. It’s like the variance is smuggled into a steady trend.

It’s a noisy table. At best maybe BITO and MSFT conform to my expectation. In fact, the broad indices (SPY, QQQ, IWM) and SPY sector indices (the “XL’s”) seem to have an even lower VRP when the trend ratio is highly positive. Considering that the market is up substantially from a year ago, the trend has been positive which tends to correspond with vol dampening option selling. This can push down the VRP via the numerator. Algebraically, it implies IV is well below realized vols that are computed using weekly sampling.

I did not expect this. My intuition is mostly tuned on commodities. I don’t see my hunch turned on its head there, but I don’t see a relationship either.

I have another idea. Since each name has its own mean VRP, let’s redo the table where each cell is a diff from the name’s own mean VRP.

I’m getting the same feeling from this table especially in those broad indices. When the trend ratio has been much greater than 1, the VRP nosedives below its average. My suspicion is the vol is getting trashed on those steady “frog-in-the-pan” rallies.

Since the trend ratio is positive, the VRP based on the weekly sampled vol is even lower still!

This begs the question…were the options therefore cheap?

Trend ratios and lagged VRP

One way we can assess if the options were cheap is to look ahead in time to see if the realized VRP was less than 100%. In other words, did the realized vol that prevailed the subsequent month outperform the IV? We call this realized VRP a lagged VRP.

[Lagged VRP was a core topic in last week’s the option market’s point spread]

This table once again partitions by trend ratio but now it displays the subsequent lagged VRP.

We do notice a preponderance of green amongst the XL sector indices suggesting the realized vols did in fact perform well vs the seemingly cheap IVs we spotted earlier.

But we did not see this hold for the broader indices. It also doesn’t mean that the IVs were absolutely cheap — after all, the lagged VRP’s on average are still higher than 100%…these options turned out to be fairly priced vs the subsequent realized vol.

Overall nothing stands out as blatantly interesting. At the same time, the non-finding, is also not a dead end. This exploration is incapable of being conclusive. It’s a year of data in 43 names with overlapping windows which means it’s not much data at all. Furthermore, the sample sizes in these individual cells is also small — sure when the XLU trend ratio was between 1.5 and 1.6 the options turned out to be cheap the following month but how often did that happen? That could be a sample size of 1. FXI and URNM never even experienced a trend ratio greater than 1.6.

Wrapping up

Like the last post, this was a demonstration of how to explore a vol idea. We started with the premise that realized vol measures can be a poor reflection of what an asset’s future volatility might be because its sensitive to the sampling period.

By choosing a different sampling period (which is what we effectively did by partitioning by trend ratio) we change the VRP which means changing how cheap or expensive the options appear. Then we see if our adjustments singled out vols that did in fact turn out to be mispriced.

There are so many parameters to play with. These were just a few from this post but you can imagine so many more:

  • Realized vols from different sampling periods
  • Different ways to compute realized vol (close-to-close vs range aware computations)
  • Any number of implied vols you can choose from the surface.
  • Asset classes, sectors, individual tickers

Personally, I start with ideas that make sense. If I measure realized volatility in 2 different ways and get vastly different numbers, it seems possible that the market might blend them incorrectly. Seems like a good place to look.

[💡General observation: The downside of an interpretable hypothesis, is you’ll probably have company. There are quant funds that generate signals they don’t even understand. The downside is when it goes wrong, it’s harder to troubleshoot. But at least nobody else is likely to find the edge while it persists.

In any case, that style of trading sounds like alien hunting. I am incapable of putting myself into the mind of alien to understand what it might do so it’s not a sport I’d think to play.]

case study on becoming a partner at a trading firm

Today I have a great read for both professional and retail traders. By another “Kris”.

Kris Longmore at RobotWealth (many of you will recognize that name because of his terminally online collaborator @theRobotJames) published:

How I Built My Trading Business as a Finance Outsider: A Case Study (63 pages)

This mini-book is so good because of the raw honesty, reflection, tactics, story, and because it’s a rare play-by-play of what it looks like to go from not even knowing what you don’t know to zeroing on on the right ways to think about trading. It’s just outstanding. Takes less than an hour to read. Much less if your in brain is in airplane mode.


The full version is fun to read and worth it but since I snip excerpts you may as well have’em:

Making all the beginner mistakes

Along the way, my friend started talking about “mindset” and “keeping a trading diary.”

The idea was that the key to trading was having the right mindset and controlling your emotions so that your biases and perceptions didn’t interfere with the serious business of interpreting price patterns in real time.

I even read a book devoted to this very topic.

And this was when the alarm bells started going off so loudly that I couldn’t ignore them anymore.

The unsaid premise of the book was that there’s some sort of objective truth in these made-up technical analysis patterns, if only we could see through the noise and take it all in effectively.

That our single biggest battle is to get out of our own way in responding to them.

That the key to trading profits is to deal with our emotional baggage.

Literally the entire book was dedicated to emotional control in pursuit of responding to these signals effectively. It seemed to be saying, “If you can master yourself, you will see the matrix and make loads of money.”

The reality is that mindset does play a big role in trading. But it’s much more boring than you might think.

Primarily, you need the discipline to turn up every day and follow boring processes without having a boss to crack the whip. You also need to have the ability to not believe your own bullshit and to think deeply about the assumptions you are making.

I’ll have much more to say about these aspects of mindset later. But let’s move on.

While reading this book, I remember having a light bulb moment where I was like, “This is insanely, incredibly, and undeniably stupid.”

Chapter 2: The backtest cycle of doom

The answer was so obvious I barely even thought about it – backtesting!

In hindsight, I wish I’d thought about this a little more deeply, instead of buying into the assumptions implicit in those trading forums and books I’d buried myself in.

The lesson this person had learned was “the importance of backtesting my strategies.”

And so my brain connected backtesting with the work of actual hypothesis testing – even though this, too, turned out to be complete bollocks.

Maybe I was just letting hope and ambition interfere with clear thinking again. After all, backtesting is an entirely technical problem, requiring little to no nuanced thinking or decision-making in the face of uncertainty. You just write some code that simulates your trading rules and get your answer.

That doesn’t mean that it’s trivial. Backtesting takes work and technical skill.

But it doesn’t require wrestling with difficult problems – problems that don’t have a clear-cut answer and require weighing up evidence and dealing with uncertainty.

In that sense, it’s easy. And I was being seduced that I could “solve trading” by doing something easy.

Example of backtesting is not research:

I’ll describe the system I set up, even though today, this makes me absolutely cringe.

I had this idea that currency markets would see most of their trading volume in the business hours of the specific currency and thus be most likely to move at those times. For example, that the Australian dollar would move most during Australian business hours.

So I created a system that would calculate the range that, say, AUD/USD moved in outside of Australian business hours, and then traded it during Aussie business hours in line with the longer-term trend.

For example, say AUD/USD was in a longer-term down trend, I would sell the pair when it broke out of its overnight range to the downside.

I had no real economic basis for thinking this might be a real effect. And there are hidden assumptions littered all through that description that it didn’t even occur to me to dig up and critique.

I now know that I was looking at it all wrong – trading is not about something being “likely to move” – trading is about buying stuff cheap and selling it rich.

A better way to look at this trade would be to ask under what conditions is the AUD likely to be cheap? When is it likely to be expensive?

A subtle but important difference.

I won’t go into a ton of detail here, but this paper is a good example of looking at the trading problem in a sensible way.

Compare the description in the abstract, where the author describes a risk premium for holding certain currencies at certain times, with the description of my system above. One has a plausible basis for when currencies might be expensive or cheap, the other… not so much.

Excerpts

As I continued to lose money, my anxiety grew.

I had no idea what was going on. The only feedback I had was my trading P&L, which had gone up quickly, but was now coming down just as fast.

Should I stop trading?

This sort of anxiety is a real problem when your only feedback is your trading returns.

And returns are extremely noisy. Even if you have a real edge, you can easily be underwater for months or longer.

Imagine having a solid edge that would make money in the long run, but turning it off because your short-term P&L is lousy!

On the other hand, if your edge has some basis in reality, then you’re in a much better position to decide whether you think it’s worth continuing to trade or not. You’re not beholden to the fluctuations of noisy, mostly random market moves.

So how do you find edges that are based in reality?

  • Think about and question the assumptions you’re making when you talk about a market effect.
  • A good question is What needs to be true for this to be a good idea? For example, for breakout to work, the market would need to trend. Markets trend when past movements predict future movements. This gives you something you can actually test.
  • When your trading P&L is your only feedback, things become way more difficult than they need to be. Have a good reason for an edge to exist.

Chapter 3: Machine Learning is not an edge

You could use machine learning to model an edge. But you don’t find an edge because you’re doing machine learning.

Said differently, you never start with the technique;

you start with the edge

In my case, I’m sad to say that I started with the modelling technique and assumed I would just find an edge.

The second big mistake was becoming enamoured with a vanity project. I was very attracted to the idea of building something complicated and flexing some creative muscles.

But if you’re serious about trading, then you need a relentless focus on things you can do to make money today.

I allowed myself to be distracted by a shiny object with an entirely unknown payoff. I was trying to solve a problem I didn’t have or even understand yet.

This is another thing that you need to flip on its head. You always start with the simplest acceptable thing and only solve the problems you have right now.

For example, don’t set up complicated walk-forward frameworks. Just split your data into subsets and see how different the factor plots look.

When you’re doing it right, trading feels like problems emerging one after another as you learn more. So, you start with the simplest thing, come up against some problems, and then deal with them.

In that way, we move forward.

You should be taking your trading way too seriously to worry about problems you don’t yet know that you’ll have. You’ll have enough real and present problems – you definitely don’t need to go find possible future ones to deal with before you need to.

Convos with professional traders

I met some people who were actually working in the business of trading – some worked in proprietary trading firms, others worked more on the institutional side. I remember there being lots of people who worked in other areas of finance who wanted to become traders.

I found that many of the proprietary trading people were surprisingly open. They didn’t talk in exact terms about things that they were trading, but we had many great discussions. They seemed to like being helpful.

A lot of these people were using Python to do research and data analysis as part of their work, but I very much came from the world of R, which I’d used extensively in my career.

Some of these people were interested in learning about R and what it could do. I was very interested in anything these people would tell me.

So I found myself catching up with these people informally and showing them some of my stuff in R. This was way back when machine learning was just starting to catch on, and people were particularly interested in seeing what I was doing in that space.

I remember proudly showing someone my machine learning framework, and they were like, “That’s really cool, but what’s your edge?”

My blank look prompted further prodding.

“What effect are you trying to model?”

Not really knowing what to say, I mumbled something about feeding returns of correlated assets into the machine to predict SPY.

“Ah OK. So you’re doing lead-lag stuff. How do you know that stuff predicts SPY?”

“I don’t,” I replied, “but I was hoping the machine would figure it out.”

It was extremely gracious of him not to laugh in my face.

This was really the lightbulb moment for me. I’m not sure why I had this assumption baked in that the past price process was predictive – if only I used the right modelling tools. But at this point, thanks to some gentle prodding, I saw how ludicrous it was to just take that for granted.

It was at this point that I became really fixated on edges and what good ones looked like.

We also had some productive conversations around what good trading research really looks like.

One conversation went something like this:

“You’ve got to remember that researching edges isn’t like the sort of data analysis you do in your regular job. The data sets you’re looking at likely have a ton of signal, and they probably don’t change much over time.”

“Financial data isn’t like that at all. It’s highly non-stationary – everything is changing all the time – and the signal-to-noise ratio is super low. Any relationship you do find will be noisy as hell.”

“That’s both a blessing and a curse. It means that your edges are going to have a ton of variance. But it also means that simple tools tend to not only get the job done, but tend to save you from thinking you can be overly precise.”

Say I’m talking to a distinguished options trader, and he says to me “Volatility has been realising significantly under implied, it’s good to be short vega here.”

Can you spot the hidden assumptions?

The first one is obvious: that if volatility has been realising under that implied by the options market, then options might have been too expensive.

I’m OK with that assumption, so long as we don’t equate it with “selling options would have made money”, which will likely follow, on average, but with no guarantees.

The other assumption is a little insidious. We tend to make it a lot without even realising we’re doing it.

Our distinguished options trader is assuming that since options were expensive in the previous period, they’re likely to be expensive in the next period too.

This is another example of autocorrelation. You could also call it persistence.

And it’s super important not to just assume it – you must look for it!

So how would you look for it?

I’m so glad you asked.

A lot of beginners, including me, would try to do a backtest or a simulation of a trading strategy and see if it makes money.

That’s nearly always a bad idea.

Backtesting is complicated and subject to a lot of arbitrary decisions, luck and path dependency (path dependency means that the results depend not just on the final prices of the assets in the backtest, but on the sequence of prices over time).

Instead, you want to move quickly and use your data more efficiently.

First, we consider what data we need.

Ideally, we would have at-the-money implied volatility of 30 days-to-expiry SPX options, and SPX returns (for calculating realised volatility).

It would take quite a bit of work to get this data. But we want to move fast. We know that disproving things is easier than proving them, and that we can always loop back if we need to.

So rather than trying to acquire the perfect data up front, we use the closest thing that’s easy to get, so that we can get moving.

The closest thing to our ideal data is VIX index data from CBOE and realised volatility calculated from SPY returns (available from Yahoo Finance and other free sources).

Once we have that data, we calculate monthly realised volatility from SPY returns. We can then compare that with implied volatility for the same month.

In summary, at a very high level, good research for trading requires the following:

  • Always question hidden assumptions.
  • Make small, testable hypotheses in an attempt to quickly disprove your ideas. Ask things like What would I expect to see in the data if this were true? What would I expect to see if it weren’t?
  • Test your ideas by looking in the data as directly and simply as you can.
  • Seek understanding, not a result. Cultivate the mindset of a curious scientist, not an engineer with the end goal in mind.
  • Favour simple data analysis tools and techniques.
  • Precision is unattainable.
  • Start with the simplest, easiest data that could disprove your idea. You can always loop back later if things look promising.
  • Learn to deal with the anxiety that you’ll never figure things out perfectly. The evidence will often be less clear cut than you’d like.

Chapter 4: My Dream Job

[a deeply personal story with loads of wisdom compacted into this chapter]

Chapter 5: Solo trading and building robotwealth

Narrowing the problem

We knew that it wouldn’t make sense to compete with firms like the one I’d worked at. We simply did not have the technology or the resources to do so.

So we spent some time putting together a plan for our trading, one that was organised around the unique constraints of independent traders:

  • Low-frequency, at least at the start while we build out our tools
  • Forgiving to trade – liquid assets, end-of-day trading

James has always been big on focussing on what you can do to make money today, given the tools and resources that you have at your disposal right now.

That means prioritising simple, obvious trades over complicated projects.

This has time and again proven to be some of the best trading advice I’ve ever received.

Things move fast and won’t look the same in the future as when you started building the things you thought you needed. And without some actual experience in the market, you don’t even know what you need right now.

And the whole time you’ve got your head down building stuff, you’re not interacting with the market. You’re not making trades. You’re not getting feedback.

If you’re building for the future, you’re not solving real problems; you’re solving future problems that you assume you’ll have.

And not only were you not learning market lessons, you weren’t making any money because you weren’t trading!

If you focus on making money today, you find yourself dealing with real problems, not problems you imagine you might have if only you can finish that backtesting framework, optimisation routine, or whatever it is you think you need.

Do something that “sucks”

Again,a simple edge that makes sense in terms of the market and its players.

But one thing that you should always ask yourself is Why would I be able to participate in this edge?

For example, if this trade exploits “predictable” rebalance flows, why aren’t the bigger, faster, better-resourced players eating up this entire edge? Why would there be any left for someone like me, trading on my laptop in my underpants on a crappy Australian internet connection?

And if you can’t answer this, or if your answer is Because I’m better/faster/smarter than everyone else, then it’s very likely that you don’t have a trade*.*

It makes sense, right?

If there’s “easy money” on the table, why on earth would the likes of Citadel and SIG leave any of it for you or me?

The answer has huge ramifications for how you think about your trading business.

The reason that you or I can participate in an edge is that there’s something that sucks about it.

For you or I to have a chance at an edge, there must be something about it that makes it unattractive to the big players. There must be a good reason for them to leave it alone or not absorb it fully. Otherwise, being the best players in a competitive game, they would leave nothing for us.

Some reasons that an edge might suck include:

  • It’s very noisy – maybe it only plays out on average in the long-term, or is very slow to converge. The big players tend to like things that give them a smooth equity curve.
  • It’s capital-constrained – maybe you can only get a small amount of capital into it before you move the market so much that the edge disappears. Such a trade might not be worth the time and attention of the bigger players.
  • It’s margin-intensive – it chews up a lot of buying power relative to its expected returns. The bigger players tend to favour capital efficiency.
  • It has a horrible skew profile – maybe it tends to blow up big time when it goes wrong, meaning you can only trade it at small size.
  • It’s operationally awkward – maybe it requires opening a bank account in a foreign jurisdiction or something equally as tedious.

You get the picture, but I’ll say it again:

All of the things that you and I can trade have something that sucks about them.

The things that tend to work in the markets also usually look a lot like “doing something useful that the market values” – just like any business.

For example, a useful thing would be to provide liquidity to traders who need to trade right now.

Another useful thing would be to trade against positioning dislocations such that you push the market towards “fair value” – this is the source of the profits from trading the futures roll, for example.

Yet another would be to trade against behavioural effects that push the market away from fair value – for example, the post-earnings announcement drift effect.

So we have this mental framework of what a good edge looks like: doing useful things that suck.

The Lab

Around 2021, we started getting interested in crypto and we were really keen to explore this brand new (for us) asset class from the ground up.

By this time, inside RW Pro, we had built out some neat collaborative research tools that we and the wider community use.

We call this collection of tools The Lab.

The Lab is all about facilitating a scalable, reproducible research effort.

It includes a hosted Jupyter notebook service connected to curated, automatically updated data sets. Research notebooks are hosted in GitHub.

What this means in practice is that I can connect to the runtime via my browser, load the latest version of a dataset, create a research notebook, and upload it to GitHub. Then, anyone in the RW Pro community can open that notebook in the same environment as it was created in simply by clicking a button in GitHub. They can run my code, take a copy, or modify it and save the changes for others to see.

Research is organised around themes that we call Research Pods.

This set up is useful for people at all levels of experience:

  • Beginners can see what proper research looks like, run the code, copy it, and experiment with it. This shortens the learning curve dramatically.
  • More experienced people can submit their own research to the community, receiving valuable feedback and growing the group’s resources.

Essentially, people get a leg up in learning how to do research for trading. Plus they get a bunch of stuff to trade, clean data, clear direction for research efforts, and feedback.

This means that for individuals, two things grow faster than they otherwise would:

  1. Your research and trading skills.
  2. The number of edges available to you to trade.

It’s a very cool concept and aims to replicate the environment you’d get in a trading firm, but for part-time solo traders.

Of course, we don’t share everything in The Lab. We’re mostly focused on low-frequency edges on liquid assets, for two main reasons:

  1. These are more forgiving to trade and don’t rely on execution skill (great for part-time soloists).
  2. We don’t cut each other’s grass too much.

James and I also trade some more capital-constrained edges, as well as some faster stuff that most people aren’t set up to do. This stuff doesn’t really belong in The Lab.

Anyway, when we got interested in crypto trading, we set up a Crypto Research Pod in The Lab, and the whole ecosystem really matured.

We used it to explore the crypto asset class from the ground up, taking many other newcomers along for the ride…

The beautiful thing is that, since the research is all connected to automatically updating data, anyone can go in there at any time and update the research with the latest data.

We also built a dashboard tool for the strategy that tracks the performance of all the factors that go into it, as well as the weights of the tickers in the tradeable universe.

We also serve this data via an API so that RW Pro people can use it in their trading applications.

As a result, we’ve had community members contribute all sorts of tools that they built on the API that help with trading: everything from Google Sheets that calculate positions and trades for manual click trading, to automated trading scripts for various exchanges and platforms, some of which I use in our own trading stack.

The crypto trading that we do today is truly the result of a team effort – entirely enabled by The Lab.

We’ve explored and traded loads of other edges with the RW Pro community as well. Some of these have come and gone over time – some we’ve retired because they seemed to die, others because we got too busy trading other stuff:

  • A portfolio of FX strategies
  • VX futures calendar trades
  • Straddle over earnings trades
  • Post-earnings announcement drift trades
  • A meta-labelling strategy for directional trading of US equities
  • We compiled a database of equity factors that can be combined into a long/short quant equity type strategy

Your greatest edge as a systematic trader – trade more stuff

This entire section on the glorious synergy of diversification is the basis of every successful professional trading org and seeing it applied to individual trading so effectively is uplifting even if it’s expected. It’s a simple idea taken seriously.

What I hope you take away from these examples is the realisation that systematic trading can work for the individual part-time trader, especially if you harness your greatest edge: the ability to trade multiple edges simultaneously.

Solo trading looks different to the world of professional trading in many respects – you won’t have the tools, resources, or the time to compete in the most lucrative areas.

But if you pick the right games by focusing on doing useful things that suck, and leverage your greatest edge by trading multiple strategies, and do the work well and diligently and consistently (and the reality is that it’s more work than most people imagine), then you can absolutely make good money as a solo trader.

Chapter 6: Lifestyle and expectations

I’ve been lucky enough to build a lifestyle that’s aligned with my goals and values. And while your goals and values will differ from mine, I can share some lessons on thinking about the sort of life you want to engineer for yourself, and what it’s really like in the trenches.

I think it’s important to ask yourself what you want from your trading.

  • Do you want to pursue a career in trading?
  • Do you want to trade for someone else?
  • Do you want to trade your own account for a living?
  • Do you want to create a part-time business that grows your capital or provides an income?
  • How much of a life outside of trading do you want?

There are no right or wrong answers to these questions, but they will have an impact on the sorts of things you’ll trade, the time you’ll need to put into it, and your performance expectations.

Some people want to do nothing but trade. And I totally respect that.

Personally, my objectives have changed over time.

I’ve gone long periods where I’ve traded every single day as if it were my last day in the markets – spending long hours doing intense work. When you’re a solo trader, you’re working on your trading business and doing the actual trading in parallel. It’s not for the faint of heart.

I’ve also taken things easier from time to time. I’ve taken time out of active trading and just run some risk premia harvesting positions so that I could pursue other projects or go on holidays.

There’s no rule that says just because you trade, you have to do it full steam ahead all the time.

It’s a balancing act and a trade off.

Sometimes an edge will come along that you know won’t be around for long, and so you whack it as hard as you can for as long as you can.

But you also recognise that there will always be things to trade, and so you don’t have to go after absolutely everything right now.

If you have the motivation and energy to do so, then go for it. But don’t think that you have to. Do it on your own terms.

it’s not all roses. It always feels like there’s work to do, but the rhythm is conducive to the life I want to live. And I think that ultimately that’s what it’s all about – doing things you enjoy that provide meaning, and bringing in enough financial support to enable that lifestyle.

Actively trading for a living is a big job.

As a solo trader, you’ll need to wear a few different hats. You’ll do the trading, do the research, manage your own data, look after business administration, and a bunch of other things.

In that respect, it’s harder than professional trading where you have a team to do the things you’re not good at or don’t want to do.

You also need to be prepared for some boring work. Trading is less glamorous than most people think and more of a grind. A lot of it is running processes and not messing up.

Be realistic about your return expectations, and don’t expect to quit your day job in the near future. Having some sort of regular income is a great offset to the reality that trading income fluctuates and is highly uncertain.

There are other upsides to teaching and running a membership business as well.

When you explain something to someone, you’re forced to really understand it on a deep level. When someone asks you to explain something in a different way, you come at it from another angle, again deepening your own understanding.

In addition, through our membership community, I’ve been privileged to form relationships with people I’d have never otherwise met. Trading solo can be a lonely existence, so having access to a community of likeminded people has made a huge difference for me. You can’t put a price on that.

Some social media gurus sell confident answers to trading problems. They make it look like you can make a quick, easy buck trading.

That’s almost never true.

Someone long ago told me that trading is the hardest way to make easy money.

This rings truer than ever.

The reality of trading is that it is messy and complex. There are no rules. No right answers. Only trade-offs and varying degrees of uncertainty.

It takes a special kind of maniac to trade solo.

It takes the kind of person who finds this reality much more exciting than the simple, confident answers some would have you believe.

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.

Moontower #249

Friends,

A few things I’m reading:

  1. The working draft of the scientific and pedagogical foundation of Math Academy. It’s free in pdf format if interested. I’m giving a small talk about MA at my local social club this week. A few weeks ago I published Principles of Learning Fast, a distillation from Justin’s blog posts which turned about to be popular. (I thought this would be more like a nerdy side-quest with narrow appeal but it turns out many of you were also gripped by it. I mostly stay away from culture topics and stick with things I’m interested in so I’m often surprised by what lands from the leftovers.)

     

  2. The Buried: An Archaeology of the Egyptian Revolution by Peter Hessler

    In 2011, we booked a large family trip to Egypt (17 people!). We canceled within a few months of travel because of the Arab Spring (since everyone had already secured the time off we audibled into an amazing African safari vacation including visits to Capetown, Krueger National Park, and Zambia where I got to take a microlight flight over Victoria Falls which is would be totally out of the question for me today given the progression of my fear of heights).

    About 15 of us are headed to Egypt for Thanksgiving so this book is my prep. I’m only 50 pages into it and it’s fantastic. Not just the content but the writing style. Beautiful and gripping. I can see why it received the acclaim it did.

  3. I just finished REWORK. My favorite parts are highlighted in Excerpts from Rework. They make for punchy reading and offer a lot to think about whether or not you’re part of a larger org. It’s organized by the chapter titles (chapter are often just one page) and the blue toggles are the ones where I added resonant excerpts. As a reminder this summer I published a doc called The Culture of 37 Signals:

    the software company best known for making Basecamp, HEY, and ONCE; writing business and software books (Getting Real, REWORK, REMOTE, It Doesn’t Have to Be Crazy at Work, and Shape Up); and inventing the Ruby on Rails framework.


Money Angle

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.

Money Angle For Masochists

Last week in the masochism section 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.)

 


From My Actual Life

On Thursday I attended and had a chance to talk to Ricki Heicklen’s Quant Bootcamp. There’s just nothing like this. It’s ridiculous. Unless you get an internship at Jane St, this is the closest glimpse you are going to get to how they (and a few similar firms) think.

If you get a chance, do it.

 

Stay Groovy

☮️


Moontower Weekly Recap

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.

the UI is gonna change

I’m going to indulge some very light futurism today.

First a quote…

…how much of their understanding of the future ultimately stems from a deep-seated need to believe that their times are important because they think they themselves are important, or want to be. — Freddie deBoer

This is an excerpt from Scott Alexander’s rebuttal to Freddie deBoer (2 writers whose Substacks I enthusiastically pay for).

Alexander’s rebuttal is titled Contra DeBoer On Temporal Copernicanism.

The gist: Freddie is nonplussed by any suggestion that our current era is deserves distinction on the historical timeline. Alexander thinks he’s wrong.

I won’t spend time on it, but the post is worth reading. I’ll just say that I am more in Alexander’s camp and have been for quite awhile but just as any discussion of financial time series is sensitive to lookback windows, if we zoom out enough Freddie gets the upper hand but in a “what are we even doing here [or anywhere]?” kind of way — we’re all dust and even the sun’s light switch eventually gets flipped off.

But zooming out so far as to make any chart a straight line is also pointless. I’d rather entertain the possibility of mattering, from which we can then find the will to talk magnitudes.

“Exponential age”, “accelerating rate of change”, this really does seem different. The world’s population, infant mortality (and therefore human lifespan), and access to space had a step-change in the past, I don’t know, 10 generations or so. The printing press was a big deal. As were boats. But the real step changes were fossil fuels and fertilizer.

Carbon and nitrogen.

Sprinkle in some scientific method and the world’s DPU are shortening at an accelerating pace.

A DPU is a whimsical term — “die progress unit” — coined nearly a decade ago by writer Tim Urban.

take the time machine and go back the same distance, get someone from around the year 1500, bring him to 1750, and show him everything. And the 1500 guy would be shocked by a lot of things—but he wouldn’t die. It would be far less of an insane experience for him, because while 1500 and 1750 were very different, they were much less different than 1750 to 2015. The 1500 guy would learn some mind-bending shit about space and physics, he’d be impressed with how committed Europe turned out to be with that new imperialism fad, and he’d have to do some major revisions of his world map conception. But watching everyday life go by in 1750—transportation, communication, etc.—definitely wouldn’t make him die.

No, in order for the 1750 guy to have as much fun as we had with him, he’d have to go much farther back—maybe all the way back to about 12,000 BC, before the First Agricultural Revolution gave rise to the first cities and to the concept of civilization. If someone from a purely hunter-gatherer world—from a time when humans were, more or less, just another animal species—saw the vast human empires of 1750 with their towering churches, their ocean-crossing ships, their concept of being “inside,” and their enormous mountain of collective, accumulated human knowledge and discovery—he’d likely die.

And then what if, after dying, he got jealous and wanted to do the same thing. If he went back 12,000 years to 24,000 BC and got a guy and brought him to 12,000 BC, he’d show the guy everything and the guy would be like, “Okay what’s your point who cares.” For the 12,000 BC guy to have the same fun, he’d have to go back over 100,000 years and get someone he could show fire and language to for the first time.

In order for someone to be transported into the future and die from the level of shock they’d experience, they have to go enough years ahead that a “die level of progress,” or a Die Progress Unit (DPU) has been achieved. So a DPU took over 100,000 years in hunter-gatherer times, but at the post-Agricultural Revolution rate, it only took about 12,000 years. The post-Industrial Revolution world has moved so quickly that a 1750 person only needs to go forward a couple hundred years for a DPU to have happened.

We have weapons of total self-annihilation.

Human industrialization in the past 200 years is changing like the entire climate and stuff.

For better and worse, modernity has unlocked the final boss and it’s us.

[At least from a human perspective — the continuity of a rock with an iron core orbiting the sun is indifferent to this stage of power. And even if it weren’t we are but one planet in one galaxy.]

I’d rather feel like the dust that I am, rather than think we live in especially interesting times. Who needs the kinda pressure that comes with a red button or even the prospect of immortality?

On the flipside, I find myself unalarmed or even optimistic about some technological concerns that some would call a crisis.

what’s been on my mind

If the rate of technological change is accelerating, the frame rate of our lives as a movie is also accelerating. Meaning any single snapshot that we use to anchor our beliefs about society (insofar as society is steered by prevailing technology) shutters faster.

For example, the fact that we are glued to our phones has led to a spectrum of concerns ranging from justified to breathless exaggeration. I liken these concerns to a cold night. We don’t want to freeze to death so we need to address the acute matter of getting through it, but it will also be over soon enough.

Let’s back up for a sec.

I got my first email address in college a generation (and then some) ago. If you have a kid graduating HS this year, your baby was born before there were smartphones. Facebook was just a website.

This whole technology of hyper-connectedness is adolescent. The entire UI is going to change. Sure those Google glasses didn’t take off and the vision pro looks like a glossy diving mask. Plus the phone being a supercomputer, GPS, camera, and oh yes, a phone has made it hard to topple for the price. But whether it’s brain-interface-enabled telepathy or something we don’t know about yet, the UX/UI of everything around us is interim technology.

I don’t read enough sci-fi to pretend to understand singularity. But I don’t think you need to build a bridge that far to see hyper-automation in the near-ish future. When I use LLMs I wonder — how long before this thing just ingests everything about me, the way Google already has, and just book a weekend trip that it’s 98.7% sure I’d love. It finds a bargain, it cross-references that I have nothing on my calendar, optimizes which credit card it books with, and even orders a fedora to keep it festive since it knows I always think it would be fun to rock one but never remember to shop for it (and it can competently project which one best matches my hue).

While this exact thing doesn’t exist yet, the precursors are here. They’re called AI agents. I don’t know if you are gonna have 5 or 500. I don’t know how finely-tuned or general purpose they’re going to be.

[You should check out Zvi’s post about Anthropic’s computer use capability. This was a functionality I was thinking was more like 6-12 months away but alas it’s here, warts and all.]

It’s gonna be weird at first, and then you won’t remember life without them.

The promise of agents combined with multi-modalities (voice, computer vision) feels like it may actually reduce how much time we spend trying to get scoliosis in front of a screen. Our whole not-looking-up existence is the technology toddler phase. It’s gonna end. And good riddance because it ain’t even cute.

The shape of consumer tech’s future is still out-of-focus, but I’d be surprised if the way we interface with information didn’t transform dramatically by the time a kid born today goes to college.

Since I’ve had this idea of “the UI is going to change” on my mind, I was delighted to find one of Patrick O’Shaughnessy’s podcast recent interviews titled “The Agent Era”. He interviews Bret Taylor who has one of these CVs that makes you think he lives on Venusian time. It’s worth a listen if you are interested in AI or agents. The excerpt I grabbed below however is not about that all.

🎙️The Agent Era (Invest Like The Best)

Bret Taylor is the co-founder of Sierra and chairman of the board at OpenAI. We cover his legendary experience rewriting Google Maps in one weekend, the myriad applications of AI agents beyond chat bots, and the one question every company should ask itself.

Patrick
How do you keep yourself from being overwhelmed? I know that you care tremendously about your family and spending time with them. You’re building an ambitious business that requires intensity, which often equals time. You’re an important player in other huge businesses like Shopify and OpenAI. That’s a lot going on. And I’m sure you love it all, which is a big reason that you do it and you get to learn at a crazy pace. How do you keep the dam from breaking with all that responsibility and all that action?

Bret
I’m not sure I’m perfect at it, first of all. I think I am, like many, focused and intense people, not perfectly balanced in always nor do I really try to be. I always think that people’s strengths and weaknesses are often strands of DNA. They’re quite intertwined. One of the things I try to do is recognize my own strengths and weaknesses and to try not to fight gravity. I am who I am, but broadly, to answer your question on how do I attempt to try to buy find balance is intentionality.

So I think that especially in the age of push notifications and e-mail, often you can let your interactions with others define how you prioritize your time. That’s a choice. If you’re going to choose to be inbox zero, that’s a choice. It’s a completely rational choice, by the way. But your time is going to be a function of how many people are sending you e-mail. So you’re not in control of that time. Similarly, if you have a really intense job, and you want to have dinner with your kids, have dinner with your kids. It’s just a choice.

You can go home or not go home, but you can say, yes, to dinner meeting or no to a dinner meeting. One of my mentors, Susan Wojcicki just passed away and was famously would never take a dinner meeting, so she could be home with our kids and was one of the most powerful executives in Silicon Valley. I would just say that I think a lot of people present things as choices not available to them, and I’m not trying to be insensitive to the power hierarchy of where you work or anything like that, but everything is a choice.

So I really tried to be self-critical and accountable with the choices of how I spend my time, trying not to pretend that anything is not a choice. You can quit any job. You can abandon your family. Probably, neither was something that most people want to do, but everything is a choice, so I tried to not let the world happen to me. It’s taken me a long time to get good at saying no. It still feels painful, but I’ve gotten better at it, so intentionality is the short answer.


In the spirit of asking a bailiff for a bobby pin, I asked ChatGPT:

what are the second order effects of AI agents for consumers?

It kindly obliged:

Second-order effects of AI agents for consumers are likely to be profound, with changes rippling beyond the immediate benefits of convenience and personalization. Here are a few anticipated areas:

1. Shift in Consumer Autonomy: While AI agents simplify decision-making by automating purchases, scheduling, and even investing, they also centralize decision-making power. As AI agents become more reliable, consumers may delegate more choices to them, potentially reducing their autonomy over time. This could lead to a reduction in critical thinking about purchases and diminish the value placed on personal preferences, as they are increasingly influenced by algorithmic suggestions.

2. Market Reshaping and Monopolization: AI agents may prioritize recommendations from companies that meet certain criteria—either by exclusive partnerships, data accessibility, or specific optimization techniques. This could skew markets in favor of businesses that cater specifically to AI agents, consolidating market power and creating barriers for new or smaller businesses that lack the resources or influence to integrate with popular AI platforms.

3. Privacy Trade-offs and Behavioral Profiling: AI agents inherently require vast amounts of consumer data to provide tailored recommendations. Second-order effects include deeper behavioral profiling and more comprehensive data collection, which could be exploited beyond personalization—for instance, in insurance pricing, credit scoring, or even legal proceedings. While it may lead to convenience, this level of data sharing could foster a loss of privacy and increased exposure to behavioral nudging.

4. Labor Market Disruptions in Consumer-Facing Roles: AI agents could dramatically reduce the need for customer service, sales representatives, and financial advisors by automating these interactions. While this improves efficiency and reduces costs, it may also eliminate jobs in these sectors, impacting individuals employed in consumer support roles.

5. Dependency on AI for Problem-Solving Skills: As AI agents handle complex tasks and provide instant answers, consumers may become less equipped to navigate challenges independently. This reliance might erode critical problem-solving skills, as people come to rely on AI for decision-making and troubleshooting. Over time, this could impact education and training as society adapts to reduced demand for certain skill sets.

6. Shifts in Consumer Expectations and Satisfaction: As consumers get used to seamless, highly personalized service, expectations will rise, leading to frustration when these high standards aren’t met. This could alter perceptions of customer service, with traditional companies facing challenges in competing with AI-enhanced experiences, pushing them to adopt AI or risk customer dissatisfaction.

7. Ethical and Societal Implications: AI agents will encounter ethical challenges—deciding what recommendations to prioritize, navigating conflicts of interest, or making potentially harmful choices based on data patterns that lack context. The spread of these agents could necessitate new ethical standards or even regulatory oversight to ensure consumer protection, as misuse of these agents could lead to financial loss, health risks, or emotional impacts.

The secondary impacts of AI agents will require consumers to carefully consider the trade-offs between convenience, autonomy, and privacy, reshaping societal norms around technology and personal agency.