Moontower #296

Friends,

If you are on X or just do a lot of investment-reading online, you are quite aware of the “$140k of income is the new poverty line discourse”.

Mike Green kicked it off with probably the most viral Substack post of the year:

My life is a lie: How a Broken Benchmark Quietly Broke America (Yes, I Give A Fig)

Of course, there are critical counters:

Criticisms notwithstanding, the article struck a nerve, so naturally finds thousands of supporters. I link to Adam Butler a lot, so here’s an example of his:

Marking the Household to Market: Why Mike Green’s $140k Benchmark May Be Conservative

And the article has been picked up and commented on by major media outlets as well. Nothing attracts a crowd like a crowd.

I thought the article was good, even if I reject the blunt claim that $140k of income is the poverty line. The article is trying to grapple with the American malaise from an economic and cost-of-living point of view. It’s hard to disentangle economic opportunity from any discussion of culture. Chris Arnade has a uniquely interesting voice on these issues, given that he’s been literally doing the footwork for over a decade on the ground (see Why are Americans Unhappy?). Green himself has pointed to Peter McCormack’s Nick Fuentes vs The World – No Country for Old Rules which centers more on the theme of a broken promise between generations. I personally find Kyla’s writing in 2025 to be exceptional with respect to diagnosing the Gen Z condition. See her recent post Everyone is gambling and nobody is happy.

I got nothing rigorous or data-driven to add. This is no obstacle to shooting from the hip. Let’s make it personal.

Immediately after reading Green’s article, I texted my mother.

The median household income in the US in 1990 was $29k or about $70k in 2025 dollar (source DQYDJ). It was about 30% higher in New Jersey. Our household income was $40k. Solidly middle class.

What did that mean?

  • We had 1 car, a 1980s Dodge Lancer that we bought used. Brand new, they were $12k.
  • Childcare? That’s called unpaid grandparents. When they couldn’t be there, we did have a babysitter who lived across the street who would come help my younger sister get ready for school when I was 12 (and make sure I actually woke up). She came by for about 30 minutes at a $5/hr rate. We were classic latchkey kids. Dinner time was the first occasion to see my mother each day.
  • My mother deeply valued education, but we were not in a good school district. So my sister and I went to 12 years of Catholic school. My high school was a La Salle high school, Christian Brothers Academy in Lincroft, NJ. “CBA” in the text. CBA allowed me to attend one of my years for free because my mom pleaded that she didn’t have the money. Tuition was a massive burden BUT we were able to do it and still eat.
  • We had lots of gifts under the Christmas tree every year. How? Credit card debt. But we were given nothing outside of Christmas and our birthdays, so this was prioritized. Not easy, but a choice nonetheless.
  • We went on one vacation a year. In the early 80s, it was always Wildwood, NJ or Niagara Falls but by the late 80’s we went to Florida. I even got a boogie board and we were allowed to get any junk food we wanted from the supermarket on vacation. We still didn’t really eat out, we’d stay in time-share hotels where mom could cook or we’d eat sandwiches. We went to Disneyworld, SeaWorld, MGM Studios. I saw Batman (the Michael Keaton one) in a theater in Daytona Beach. It was our favorite 2 weeks of the year.

Money issues were a cloud over my whole childhood growing up. Still, I knew I was safe and I knew I wasn’t exactly poor. If we didn’t eat our food our elders would tell us to think of the “poor” so we knew there were levels to this. Plus, I saw the Sally Struthers commercials with the African kids who don’t even swat the flies from their eyelids. It took me 3 years of begging to finally get the bike I wanted, but I eventually got a bike.

In general, I knew that it would be selfish to ask for things because we were constantly reminded that money was scarce. In Catholic school, I felt like I had less than the other kids on average, although I’m sure there were some kids in the same situation as me. As I got older, my awareness of this grew. The bar to think someone else was rich was low. Did they have a pool, even above-ground? A second car? Did they get Skidz or Cavariccis when they were popular or long after they went out of style?

It’s extremely clear what my mother’s financial algorithm was. Budget ruthlessly while prioritizing what she thought were a few must-haves:

  1. education
  2. vacation at the beach (this is universal across my family and I wonder if there’s an Egyptian undercurrent to it)
  3. And specifically in my immediate family, Christmas gifts. I had a sense not only that my mother loved us, but I think she wanted us to have a concentrated moment of joy, even if it was once a year. She was hard on us, at least compared to how we saw “the American kids” get raise,d but Christmas always felt a bit extra. Like she was saying, “I know it’s hard around here most of the time, but life is supposed to have joy. You’re not brats and I see you. This is our little deal. Bear with me the rest of the year and I’ll make it up to you.”

The point is, being middle-class is hard. You cover basic needs and triage just a few wants. There’s very little slack. If mom loses her job, does the credit card debt bury us? Look, my parents split. Mom gave dad what little money she could afford out of sympathy. He had nothing, his single-livery-car business going bankrupt a few years earlier than he went bankrupt personally after a short time on his own. It’s all so precarious.

But it is obviously precarious. So much so that you burn with desire to escape it. By the time I was in high school, I knew I wasn’t going to live like this when I got older. I’ll do whatever pays because I know this sucks as a state-of-being, even if it’s not destitution. This is my hot take — there was nothing ever comfortable about being middle-class. It’s not supposed to be the basin of an attractor curve. It’s a transition to a better life or moment during a freefall. It sucks to be middle-class according to these articles. Well, guess what? It sucked 40 years ago, too. And if you are in it, the only thing you should be doing is trying to escape it.

The literati, finance-footed, and cultural observers go on about the plight of the middle-class — causality, diagnosis, comparing what life is like for those in the middle-class. That’s fine in some academic, sense-making context. Maybe it’ll even affect policy. But this is all you need to know — being middle-class sucks. It will always suck. And all the discussion about it is under some guise that if we [insert policy] it won’t suck OR to make you feel that the plight is exaggerated. The first is lie and the second is patronizing.

Poor people don’t need to be told it doesn’t suck as much as they think. Poor people don’t think there’s some intervention that will make being poor suddenly acceptable. They just want to be unpoor. It would be adaptive to adopt that mindset if you are one rung away from being poor, too.

Am I being harsh? I think I’m just being realistic, but I know it sounds harsh. My perspective is meant to be individually pragmatic because there’s never going to be rest for the middle-class as a cohort. As pointless as they feel, I have my sympathies. When I was growing up, I believed that through education, I was going to escape. And with reasonable odds. Like being top 5% in my class was a sure ticket to a better life. Not easy, but an amazing payoff reliably predicated on effort and persistence.

Today, there is a profound sense that you can do “all the right things” and that only earns a ticket to a capricious, opaque lottery. College application stress in 2025 is societally pathological. Meanwhile, on the backside, new grads face cloudy prospects and high living costs.

Being middle-class sucks. To be stuck in it without a legible path out is but a dormant revolt. “Do everything to be in the top 5% and escape” vs “do everything to be in the top 5% to be allowed to enter a lottery with a 5% hit rate” is a giant deterioration of the American bargain in just a single generation.

To wrap up, remember, it may sound self-contradicting because the middle-class is defined by centrality and encompassing the masses, but it’s not a place to stay. The resolution of the statement is dead simple — being average stinks. It always has and it always will. You might find solace in the fact that being average here is better than being average elsewhere. But you’ll probably stay average if that’s of any comfort. The world is indifferent to an American’s complaints. The human condition reminds us that it is a luxury to be heard. Accept that and act accordingly.


Money Angle

I keep adding calculators and tools for your use and education here.

This week, you’ll find a new American Options Early Exercise Calculator. It works for both calls (for dividends) and puts (for interest). Education is embedded in the documentation.


Ethan Kho host of the terrific Odds On Open podcast published our chat. The YouTube comments give high praise, but one of them accuses me of being drunk. I remember being on only a few hours of sleep that day, but bruh, drunk? C’mon. My fault for reading the comments.

Money Angle For Masochists

I also whipped up this calculator in response to a question I am asked often — how do you weight the legs of an option trade? Again, the education is embedded in the documentation/links.

Option Pair Trade Calculator


Benn Eifert’s Options Threads

@quant_spence compiled a document of all of Benn’s threads and interview snippets with respect to options. If you don’t know who Benn is, you are in the wrong section of this newsletter.

Benn’s Option Thread of Threads


Coastline

I’m boosting Thursday’s article once more because even if you aren’t interested in options but just returns and volatility, it will get your gears turning, which is always good for some inspiration on how to think about risk, sizing, and measurement broadly. Plus who doesn’t like a good ol “how do fractals relate to markets” section.

The Coastline Paradox in Financial Markets


Webinar

Quant Insider is hosting a live webinar this morning:

Systematic Mean Reversion & Cointegration: From Statistical Tests to Trade Execution

Moontower readers get 50% off with this coupon.

 

 

Stay groovy

☮️

Moontower Weekly Recap

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Moontower #295

Friends,

First of all, here’s the slides I shared in this vid:

I hope that video was helpful. I watched it again because I think the topic is complicated, not technically, but because it’s counterintuitive. Trades like that were bread-and-butter through my pro career (and very much why I “spotted” it despite it not sticking out in the tools other than the Trade Ideas filter which is highly validating of our algorithm! I’ll allow myself to be happy about my own work for 1 second. Ok moment’s passed, let’s continue.)

Before we head on to Money Angle stuff I’ll share 2 things I enjoyed.

Fermat’s Last Theorem Documentary (link)

This 45-minute video follows the story of Andrew Wiles’ quest to prove Fermat’s Last Theorem. I didn’t know the history of the theorem or even what it stated. It claims that for any whole number exponent other than 2 there are no values of A,B,C that would satisfy Aˣ + Bˣ = Cˣ. You can’t prove this computationally because there’s an infinite number of possibilities. The proof requires mathematical logic.

Fermat allegedly had a proof but hadn’t written it down. Turns out Wiles’ proof would have been impossible for Fermat to have known (this will make sense when you watch it). Anyway, I loved it. Yinh fell asleep. YMMV.

Holiday coziness — games!

I taught both my boys backgammon this past week. This is the younger guy playing with mom.

I used to play a lot with my colleagues during the year I was a broker on the NYSE floor. Every time I came back to the “booth” (that’s the area with the phones on the sides of the exchange floor where clerks take orders from customers), I’d make a move on the Jellyfish software. When I was at Parallax, I worked with 2 of the best backgammon players in the world (one of them was the best in the world iirc) and Parallax was actually founded by Roger Low, who was a world-class player himself. Roger had retired by the time I joined so I never got to know him.

Backgammon is especially neat if you like options because the doubling cube begs you to price volatility.

💡Fun fact

When I had my phone interview with SIG (this is the round that happens in between campus interview and the final on-site) I was asked a basic question regarding the cube. Since accepting the cube doubles the stakes of the game and rejecting it forfeits the current value of the game, what is the minimum probability of winning you need to accept it?

When looking at the board you need to evaluate how risky the position is. Like how likely is the tide to turn? When you offer the cube you are selling your opponent an option and its value depends on their chance to come back. But if you offer it to them when they have no chance they will reject it and be bailed out because you have now sacrificed your own possibility of getting a gammon (double points) or backgammon (triple points) if you beat them by a large margin.

It’s a great game for kids because they get to practice dice math. I was playing last night and knew I’d win as long as my next roll wasn’t a [1,1], [1,2], [2,1], [3,3]. So the kids would first need to figure out that’s what they are rooting for and then I ask them the probability. 4 out of 36 or 1/9. Plus the little guy figured out that the 7 is the most common roll and how to count the number of ways to get each number (he was delighted by the pyramid pattern when he realized it).

We always play more games during the cozy holiday season and I’m irrationally pleased that this season it’s backgammon. I recommend it.

[Also, if you are just learning, play a bot on your phone. You learn the game very quickly getting trounced by bots. Ultimately, I’m just a casual player, I never studied it, but would just play for $5 a game with my NYSE squad. Of course, with the doubling cube and possibility of gammons that can multiply pretty quickly. The real hitters play for four and five figures per game.]


Money Angle

On Nov 26th, Imran asked his followers would what more likely to double in the next year — gold or BTC?

I looked at the result of the poll just a few hours after it was posted and it was BTC 52% to gold 48%.

By the time the poll closed with 750 votes, BTC had garnered 2/3 of the votes.

I don’t know if me a jerk had anything to do with this but when I saw that the vote was almost a coin flip I chimed in.

Focus on the last part.

The poll should be nowhere near 50/50 because you would be able to lock in a great trade by selling gold in this proposition, buying gold call spreads financed by even more expensive BTC call spreads.

This is a classic difference between markets and democracy. It’s a perfect example of the Dinosaur Markets post in real life. The markets in the options reflect the volatility and the cost of replicating these bets. Money-weighted votes are interested in the truth where opinions are cheap as sand.

It’s very difficult to have opinions that are above replacement value about liquid assets. If you’re truly good at this, then being Scrooge McDuck rich based on consistently betting on these fantastic opinions is the only proof of such a skill. Few people are rich because of a crystal ball.

good way to make a living in finance is to find the people that voted for gold in this poll and offer to trade with them. You need to do this in the dark because if you tried to do it on a public exchange, you’d be undercut by traders competing to sell the gold proposition to these opinionated people and it would drive the price down to a non-arbitrageable price.

Public markets protect overconfident people with arbitrageable opinions from their own ignorance and stupidity. Private or non-transparent markets are nice ways to shove a vacuum hose into their bank account.

There are many places where there’s alpha in projecting your opinion. This is the stuff you spend your time on in life. Where you have self-knowledge, private info, competitive advantage, skills, taste and so on.

But when it comes to markets, remember what we learned here just a few weeks ago:

the arbitrage reflex is more profitable than the opinion reflex

 

Money Angle For Masochists

Let’s continue on the same theme because these threads are going to become far more frequent for anyone who cares about markets. “Thinking in Bets” has a long runway, the way this country is headed, before it jumps the shark, so you might as well get used to it. From “Everything computer?” to “everything casino?”

Prediction Market Arbitrage: Using Option Chains to Find Mispriced Bets

Horse tweeted:

The moment you see a bet on a platform like Kalshi, Polymarket, or the soon-to-be Robinhood+SIG exchange, your mind should jump to the options chain.

The tweet says the Kalshi market is pricing a 9% chance of BTC hitting $250k

The options market can offer a quick sanity check. BTC is about a 55% vol. We are just being very approximate so not worrying about the term structure. I just want to show you my automatic mental response to the tweet.

Without hesitating, I pulled up the calculator on my phone and entered:

ln(250k/89k) / (.55 * sqrt(13/12))

Why?

We want to compute how many standard deviations away the $250k strike is to get a z-score which we can then convert to probability. Standard deviation depends on volatility and time. The more time or volatility you have the “closer” some percent return is. A strike that’s 100% away is extremely “far” if the asset needs to get there by tomorrow. If you have 10 years to get there, it’s not super far at all, you only need to go up 7% per year. Likewise, if an asset only varies by 5% a year, 100% is “far”, but if it moves 50% per year, 100% feels much “closer” or possible.

The formula above is simply dividing the percent return to get to the strike by the annualized volatility scaled by root(time) to find the distance.*

*Standard deviation or volatility as a quantity is proportional to the square root of time. Or you can say variance, the square of standard deviation, is proportional to time. The easiest way to remember this is to recall that when you compute the standard deviation of anything, you have an intermediate step of summing the squared deviations to get the variance, then divide by N. But to get back to the standard deviation, you take the square root of the ratio. The ratio in the intermediate step was variance/N. The final answer, the standard deviation, was the ratio of sqrt(variance) / sqrt( N)In our computations, N is replaced by time.

At the time of the tweet, BTC was 89k and there was 13 months until 2027. I assume 55% volatility.

Solving:

ln(250k/89k) / (.55 * sqrt(13/12)) = 1.80 standard deviations

We then use a standard normal table or normdist in Excel to see that 1.80 standard deviations encompasses about 96.4% of the cumulative distribution. Therefore, the probability of BTC going HIGHER than 1.8o standard deviations must be 3.6%

This is fully explained in Using Log Returns And Volatility To Normalize Strike Distances

The computation of this distance, besides being dependent on an estimate of volatility which we can borrow from the options market, assumes the asset is lognormally distributed. If you believe, as the options market certainly will if you look not at the at-the-money vol, but the far out-of-the-money call vols, that there is more positive skew than a lognormal distribution then our 3.6% estimate is too low.

But that logic is moving us in the right direction. We want to take the intel embedded in the options market when considering the price in the prediction market. We expect the liquid options market with much more volume and money behind it, to be the best guess as to the “fair price” of a proposition. If there’s an edge, it will be in the mispriced prediction market.

A prediction market bet can take a binary flavor. For example, “Probability that BTC settles above X by some date.”

It can take a “one touch” flavor. “BTC to touch but not necessarily settle above X by some date.”

Of course, “touch” is more likely than “settle” because “touch” encompasses all the times BTC settles above X, but also includes all the cases where it breaches X and falls back below X by expiry.

We can get information about the price of both binary and one-touch scenarios from the option market.

1. The Binary Bet: Price the Terminal Outcome with Vertical Spreads

Pricing: To find the true market-implied probability of the event, use the price of the spread:

Vertical spread price/Distance between the strikes ~ probability of asset expiring above he midpoint of the spread

Potential arbitrage if…the probability implied by the options chain is lower than the price offered on the prediction platform, you can buy the vertical spread and take the under in the prediction market or vice versa.

Further Reading: A Deeper Understanding of Vertical Spreads

2. The Path Bet: Account for Skew and Volatility with the One-Touch Rule

Pricing: You can estimate the path probability using the trader’s rule of thumb: take the delta of the vanilla option at that strike and multiply it by 2. This naturally takes into account the option implied skew because the delta is derived from the implied volatility at the strike.

The mechanics of an arbitrage here are complicated as it requires dynamic hedging. If that sounds interesting, perhaps you are born to be an exotic options trader. I have never tried replicating a one-touch option so while I could certainly “financially hack” a model, the main point I want to convey is that the pricing of the one-touch can be inferred from the vanilla options market.

Further Reading: one-touch

 

Stay groovy

☮️

Moontower Weekly Recap

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Moontower#294

Friends,

I really hope to be helpful today so bear with me as this isn’t the rosiest way to begin.

This tweet halted my scroll:

For whatever reason, AOL (what year is this?) has an unpaywalled copy of the article:

A Recipe For Idiocracy

It’s short, but let me pull an excerpt anyway:

For the past several years, America has been using its young people as lab rats in a sweeping, if not exactly thought-out, education experiment. Schools across the country have been lowering standards and removing penalties for failure. The results are coming into focus.

Five years ago, about 30 incoming freshmen at UC San Diego arrived with math skills below high-school level. Now, according to a recent report from UC San Diego faculty and administrators, that number is more than 900—and most of those students don’t fully meet middle-school math standards. Many students struggle with fractions and simple algebra problems. Last year, the university, which admits fewer than 30 percent of undergraduate applicants, launched a remedial-math course that focuses entirely on concepts taught in elementary and middle school. (According to the report, more than 60 percent of students who took the previous version of the course couldn’t divide a fraction by two.) One of the course’s tutors noted that students faced more issues with “logical thinking” than with math facts per se. They didn’t know how to begin solving word problems.

The university’s problems are extreme, but they are not unique.

The article drones on. None of it uplifting.

“We call it quantitative literacy, just knowing which fraction is larger or smaller, that the slope is positive when it is going up,” Janine Wilson, the chair of the undergraduate economics program at UC Davis, told me. “Things like that are just kind of in our bones when we are college ready. We are just seeing many folks without that capability.”

Here’s Jared’s firsthand experience as a teacher while quoting that article:

This should remind you of this quiz from 2 weeks ago

Victor Haghani referring to the quiz (emphasis mine):

It is well-known (and disturbing) that the financial literacy of this audience is, on average, quite low – as evidenced by a mean score of 56% (yes, that would be an “F” if not graded on a curve) on the below five-question quiz, known as the “Big Five” test by researchers. A survey conducted in 2021 found that less than one third of respondents answered at least four of them correctly, the threshold researchers define as “high financial literacy.” At least as concerning as the low test scores is the fact that the scores themselves have fallen dramatically between 2009 and 2021.

Are you seeing a pattern?

The useless question is “why” all this decline. Is it the phones, social media, microplastics, fluoride, the mentality that “kindergarten is the first step to Harvard” is less about upholding standards and more about suing teachers who give bad grades (just scroll thru the results)?

Probably all of them, I don’t know.

And then you have this response to Jared from our mutual friend:

The public discourse amplified by the rich and powerful is tuned to spread to the lowest common denominator. So the average person notices that rich people sound stupid and mistakes the mask for the face. The spread of information has also made corruption more obvious. That Trump’s favors are openly for sale is celebrated by his defenders as transparency. “They were all doing this, at least now we can see it”.

Fine.

I’ll let you keep that defense, but it’s hard to hear that without also hearing “we should all be allowed to crime”. Populism brings some unintentional equilibria I suppose. [I’m warming up to the idea of paying all politicians a salary of $2mm/year but making them truly public servants. All your financial affairs on full display. The fact that Congress can insider trade tells me we are so far from accountability with teeth.]

Adam’s observation is an instance of the current hypernym: honesty is for suckers.

Don’t get me wrong. This is a permissible instinct as trust in institutions disintegrates. But we risk some baby/bathwater mistakes if we malign all institutional failure as rot from within (university-industrial complex) rather than the natural difficulty of keeping up with accelerating times (securities regulation). Human affairs, the realm of politics and coordination, don’t move as fast the electrons re-shaping power and that impedance mismatch is a source of static. But that’s not nefarious. It’s just social physics.

That was a long digression to land me back where I was headed anyway — “be dumber” is an overfit to a moment we are all struggling to understand. It’s a retreat from responsibility. A cop-out. Hopium that there’s a quick way to get above this fray, shielded from the stray bullet from any of cultural ails lurking below the seemingly healthy SPX price.

I’m sorry but you can’t fake A yourself to flourishing. The flourishing is a by-product of the wax-on, wax-off. Confidence in your competence. Having some real to offer. There’s no “getting through this moment” because life is just one of these moments after another. So tie yourself to the mast of self-efficacy and it will all feel calmer.

If you tell me we’ve gained something from the loss of standards above, I’ll listen. But what hasn’t changed is you need something to offer. Society is not your parents. It doesn’t love you unconditionally. It’s hard to make beneficial choices if basic literacy and numeracy isn’t automatic. “I’ll just ask the LLM”. Well, knowing how to ask good questions itself takes intelligence and learning.

[Personal conviction…I think the quality of someone’s questions is a strong indicator of their thinking skills. This is pretty obvious if you spend too much time on X, but a universal example is to think about the last time a child asked you a question that had you go, “Damn, smart kid”. A know-it-all like the nasal boy in Polar Express comes off as obsessive, maybe smart, definitely annoying (although not a crime). But asking the right question reveals layers. For the finance heads, it’s why Jane Street uses this prompt in interviews — see thread. To just give an answer is to misunderstand the exercise.]

Ok, so the trends in reading and math say we are less and less prepared to engage in sophisticated reasoning. And we acknowledge that reasoning is important because it’s the basis of decisions and decisions are the bridge between our internal selves and our physical experiences and conditions.

How do we reverse the trends?

I don’t have an answer for society but I do have answers for you. And your family. And your friends. (“Hey, doesn’t that scale up to society?” That’s cute, did you just arrive from Mars?)

The answer has 2 facets and since we started in the context of math we will stick with it, but I don’t think it’s limited at all to math.

1) The belief that the process of learning itself makes you smarter

We all have potential. Just like in sports. You can’t be Usain Bolt but you can always get closer to your ceiling. We choose which domains to try to move closer to our ceilings since we can’t work on everything. We prioritize based on goals. Fitness, chess, cooking.

Math and literacy touch everything, whether you want them to or not. We are all touched by deals, contracts, transactions, even if we just want to paint. Youth is the rare stage of life where there is time carved out specifically for upskilling your general-purpose machinery of abstract thought, the manipulation of symbols, and the ability to maintain a chain of ideas inside one brain. I’m not sure if the appeal of doing so is universal, but the fact that games and puzzles are not compulsory and in fact pulled, not pushed, suggests that there is something intrinsic about cognitive self-improvement. Fostering this urge requires no justification beyond “it’s fun” but it happens to have salutory effects across your mental wetware and let’s face it, your job prospects, if you insist on being purely practical.

So this gift of time that children are afforded is when the skill of skill acquisition should be taught. I emphasize this because school is treated not as a place where we acquire skills but a place to trot them out for approval. The difference is insidious. As you traverse the years, it’s not what did you master, it’s what grade did you get? There’s really no emphasis on mastery. It’s just “did you go through the motions” for most, and then for the top students, who may or may not have achieved any type of mastery (and if they did it wasn’t to the school’s credit), the school is just a sorting hat. And with grade inflation a bad one at that, making students (and their parents) feel like college admissions is plinko.

My HS diploma-only mother emphasized school because education was the path to a better life. But she specifically stressed math because she thought it literally made you smarter. Her opinion is backed by nothing but intuition and self-flattery (she was a strong math student). But Ced, whose practice and writing is maniacally obsessed with the art and science of getting good at things and separating b.s. that sounds like it works from what actually works in complex domains, sent me a link to mathematician David Bessis’ interview with Russ Roberts:

🎙️A mind-blowing way of looking at math (Econtalker)

Bessis echoes what my little immigrant mom said. In describing what we need to do differently in teaching math, he argues we must not mince words to motivate:

I think teachers should be bold. They should say, ‘It makes you smarter.’”

More:

People hate math because they view it as an IQ test that they’re failing. And, it’s not a test. It’s a technique to get smarter.

If you’re failing, it’s normal because you start. When you start any new sport, you suck at it. There’s no way you’re going to be good on Day One. Just because a two-year-old is babbling, you don’t say: Well, I guess he’ll never learn to speak, but we just won’t bother teaching him language because he’s not good at it. And yet, we do that with math. We say, ‘Well, he’s not a math person. He’s not good at math.’

You cannot teach mathematics to kids who are convinced that your mathematical ability is something that is static… A combination of confusion about the nature of mathematics, and confusion about how the brain operates, and confusion about the origin of the shocking gap of abilities that are visible on a given day in a given high school makes us believe that this thing is entrenched and you’re not going to be able to change it. But it’s not true.

The failure of teaching mathematics—and it’s something that has been going on for not just centuries, but actually millennia—is the failure to admit that we do things in our head. We play with our intuition, we play with images, and these things have traditionally not even been discussed as being part of mathematics.

At school, you enter the room with your intuition, and the teacher is telling you that your intuition is wrong; and you reach your conclusion that intuition is bad and that you’re stupid. But, the thing is, it’s wrong, but it’s not going to be wrong forever. You will gradually evolve your intuition if you confront it with this very special apparatus that is logical formalism.

Mathematics is a technique that, if you learn how to master the technique itself, you will develop your intelligence; you will utilize your brain in a way that you would not be able to otherwise.

But this is really cutting to the heart of my mother’s hunch, which she couldn’t articulate:

I knew when I was a mathematician that what was really interesting to me was not the mathematics: it’s that kind of meta-cognition that you have to learn to become a mathematician. And this is the topic of the book. What do you do inside your head when you become better at mathematics?

It’s worth mentioning that much of the interview is spent on intuition and what Bessis, playing on Kahneman, calls System 3 thinking:

Whenever you catch your intuition red-handed being wrong at something, don’t throw that away. Don’t reject the intuition… Explore it. Try to unpack it… do back and forth until they agree. It may take you five minutes, one hour, a day, a week, a year, 10 years, 50 years.

Bessis argues that this process of confronting incorrect intuition is a uniquely valuable habit because it creates a highly memorable learning stimulus. This rings so true personally. When something goes wrong, when you are snapped out of autopilot, or surprised, the lesson you learn sticks with you.

His last inversion, namely, that math is not a test of smartness but it makes you smarter is a hokey story of being intimidated when Bessis noticed legendary mathematician Jean-Pierre Serre in the audience. After the Bessis talk, Serre said he’d need to repeat the talk because he “didn’t understand a word of it”. Serre was being sincere. Bessis noticed that most people would not admit to incomprehension so easily. And while it’s much easier to do so if you are Serre, whose capabilities are beyond reproach, Bessis wondered:

“Maybe with that attitude, you can become Jean-Pierre Serre.”

Ok, so the first step to improving our abilities in math (or literacy) is believing it’s possible and worthwhile.

The next step is to know how to actually acquire the skills.

2) Skill development is not the same as education

School is time-based education. You do X in 4th grade, Y in 5th and so forth. There’s some acceleration but it doesn’t stretch as far as individual variation because the range would be too wide to contain in a single classroom. The compression hurts not only the top performers but the bottom performers who are hanging on for dear life only to be waved through to the next grade, where the deficiencies compound.

Skill development is rooted in learning science. You are far more likely to have encountered its prescriptions in sports or music than school. I encapsulate a lot of that information in The Principles of Learning Fast. But today I want to zoom in specifically on our foundations because it’s an actionable target if you are insecure about your knowledge and how to go about learning to mastery since you may have never realized that was an option. How could you have realized that…there’s a test tomorrow you need to study for even though you don’t understand the material from last week’s test, right? It’s not your fault but hopefully what you’re about to learn can serve you and your loved ones going forward.

I’m going to let Alpha School’s Joe Leimandt be the messenger. The following flow comes from an interview he did with Patrick O’Shaughnessy.

🎙️Building Alpha School, and The Future of Education (Colossus)

1) Knowledge is hierarchical

Most of knowledge is hierarchical where it’s based on foundation. Algebra is basically advanced fraction manipulation. Fractions is multiplication and division. And you can just keep going down the tree where you have to actually learn bottom-up and have mastery.

2) Well, what is mastery?

Think of a sports analogy like in basketball. If you’re the point guard and you lose the ball 30% of the time going down the court, the coach is not going to be like, hey, let’s work on the alley-oop. They’re going to be like, okay, let’s get back to the basics and master the basics so you can get down the court.

Have you mastered the basics? How good are you? We always talk about in standard school, there’s a whole set of things that 70%—you’re passing, you don’t know 30% of the material, and then they move you on to more advanced things.

This is pretty obvious stuff. You know how this feels:

3)The Swiss Cheese Problem

The problem’s not the algebra, it’s the prior knowledge… if you’re pushing people up and they’ve only learned 70 or 80% of the curriculum, you should think it’s like Swiss cheese. It’s like you’re building a foundation with all these holes. And then eventually as you get high enough, it just gets too much and it collapses and you can’t learn anymore.

4) Going Back to 3rd Grade

If you’re doing fractions and you haven’t mastered division, you’re going to sit there and say, God, this fraction problem is really hard. But the real issue is, well, just go back and learn your division and then the fraction’s going to be easier.

We have one student who was, this is sort of a unique, an extreme example and I hesitate to say it but we had a student who was 740 on the math SAT and in looking they were making careless errors. Some of the problems they were overloading working memory and for whatever reason the student didn’t have fluency of multiplication and division tables. So we literally sent her back to third grade math.

We’re the only school in the world who will take a 740 math SAT student go back to third grade, send back and she got a 790, a 790. And it’s that kind of thing where when you talk about the science of learning and just I say it this way, the parent and the student in this case were not excited that their 740 math student is being given third grade problems. That can’t be the issue, but it is. It is, because you’re overloading the working memory and she’s just making careless mistakes.

My eldest is 12. I keep telling him that the form on his basketball shot is off. He finally asked me to show him a video of him shooting. After seeing it, HE decided he wanted to correct it. He understands it’s a step back to go forward. I gave him tremendous praise for the decision because it’s not easy to make choices like that. It’s an investment in the bigger picture

[He’d like be able to make the HS team and it’s gonna be competitive. His current shot won’t cut it, especially since I don’t expect he’ll be very tall.]

My wife is going to start Math Academy because she sees the kids’ work and, well, there’s lots of swiss cheese in her knowledge. She decided that didn’t sit well with her. The kids asked her what level of math she’s gonna rebuild from and while the diagnosttic will place her, she has no shame about however far it suggests. The 12-year-old would bet he’s ahead and she’s not taking the other side of that.

Everyone is anxious about time. Finish so you can get to the next thing and the next thing. I’m very sympathetic. Things just feel like a race. Business is often a race. It’s hard to backfill expertise or keep up with all the cool new stuff when you’re putting out fires. So I don’t know to what extent we as adults can choose mastery for ourselves. I don’t pretend to know your constraints. But when it comes to the kids, I urge you to think about this stuff. You know what it’s like to have swiss-cheese in your foundation. Holes are not totally avoidable. But rushing to check off “done” is training for a life of cramming. Of seeing a stimulus to grow as an obstacle to relaxation rather than an opportunity to expand your capacity to offer something to others.

That’s a real goal. Not a fake one. Getting there takes as long as it takes for you. But once you’re there you can’t be shaken because the foundation is rock solid. The title of today’s letter is hook to remind you:

Slow is smooth, and smooth is fast

There’s no shortcut to smooth.


Money Angle

A friend was asking me how to deal with a loved one who had put nearly all of his assets into a particular volatile stock and done very well. So far. The person is in their 30s with a family and my friend is concerned that if things go the other way this could be the type of thing the household might not recover from.

I asked the basic questions which of course my friend also asked. What’s your plan if the stock falls? “Probably buy more”.

Do you have a target where you’d be willing to sell any of the shares? “If it doubles again, I can retire so nothing before then.”

We can sit here and talk about risk management and yadda yadda. But I’m gonna share something personal which makes me think this has nothing to do with rational finance thought.

I’m close with people that have been taken in by pretty obvious scams. All the red flags. But the people I know are smart people. People that can compute an interest rate and all. They don’t tell me about the “great opportunity” because they know I’ll plead with them to not do it.

Predictably, they get burned. (I’m not supposed to know that because they don’t want to hear I told you so. But I know.)

They fall for this because they want to believe so badly that their better judgement doesn’t stand a chance. I’m totally nonplussed by this. It’s fascinating that we are capable of this. It explains quite a lot, good and bad, actually. But it’s not suprising if you pay attention.

But here’s the part that I found surprising and discovered on a lark.

In the aftermath of the scam, I spent 2 hours on the phone with a victim. I was standing in my kitchen of the last house. Beautiful day outside. Brutal conversation. Emotional. Just trying to make sense of it in a way where we could at least salvage some vague sense of growth out of the closure. At the tail end of our call, I asked a question that I still find peculiar but somehow felt appropriate:

“Did you need to lose that money?”

Silence.

I could hear them think.

“Maybe”.

We talked about it. There was nothing that could have been done. No warning I could have given would have talked them out of it. They admit to that.

I think about this a lot.

I told my friend whose concerned about their loved one this story. And the friend’s face dropped. They know what they’re up against.

(We actually came up with 2 proposals that he could bring to the loved one to change the shape of this death wish, we’ll see if either find reception.)

Anyway, as BTC has been dropping, this thread has been on my mind because there are a lot of cult leaders who benefit from persuasion but aren’t accountable to their followers’ families if they’re wrong.

I’ll just leave you with a tweet I sent Tuesday:

Sitting down at a table without a budget is a commitment to playing til you’re wiped out.

Stay groovy

☮️

Moontower Weekly Recap

Posts:

Moontower #293

Friends,

The largest firms in the world’s capex doesn’t lie. They’re all-in on AGI. Since the so-called hyperscalers are also a historically disproportionate share of the SPUs, they are dragging the entire economy into that bet.

The “dog with a mouthful of bumper” outcome is they are right and actually eat the whole economy, only to be murdered by their own bunker guards. The irony of using Sama’s ChatGPT to query this:

OpenAI’s fundraising appetite and valuation requires AGI to be a thing, whereas a company like META will survive as a going concern and may even get stronger despite the capex blowing a big hole in their balance sheet temporarily if AGI is not a thing. Yann LeCun, META’s chief scientist and Turing award recipient, is leaving the company. He’s critical of the “scaling hypothesis” which claims that if you just keep throwing compute and data at the models, they will become “intelligent”. He doesn’t see how causal reasoning would ever emerge from pattern-matching even if it’s the most superior pattern-matching the world has ever seen.

This debate feels like mommy and daddy are fighting while the family’s future hangs in the balance. The naughtier kids are using the distraction to raid the cookie jar, while the market’s spirits are a thermometer on who the rest of the kids want to side with.

In a Carlota Perez framework, the prospect of AGI would suggest we are still early in the installation phase, but if the common knowledge surrenders to” AGI is never spawning from the current soil” then we are probably already in the deployment phase but not every middle-manager has taken Prompting 101 yet. In the first case, the calls aren’t hot enough, and in the second, you want your stocking stuffed with puts. Either way, we’ll take the electricity. But Santa, gas not coal, please.

Below the sci-fi (is that science fiction or science finance?) theatrics, we have the mundane business of actually using these things. Last week I shared the listicle voting app thing with some resources for those who want to make stuff with LLMs. This week Khe had a detailed post describing a CRM he built:

Vibe coding? More like “whack-a-mole” coding: The uncomfortable truth around my Pebblr CRM app (link)

Here’s another fantastic article that I think captures nuance between AGI breathlessness and very real capabilities of LLMs today.

Is Vibe Coding the Future of Skilled Work? (Scott H Young)

It’s written from a relatable perspective since I’m using these things so much, while easily admitting they are enablers rather than substitutes. And isn’t that a sweet spot? Like you can do more but still matter? Well for now I guess. We’ll see what happens. If the puts pay off maybe that’s bullish for humanity.


I’ll share some vibe-coding projects here and there.

Here’s my Car Lease Embedded Option Calculator.

Some background for the uninitiated:


Money Angle

A traditional way to think of a stock price is the expected value of its future prices weighted by their probability and discounted to the present. Ignoring the cost of money, in a binary world a $100 stock could be fairly priced if it was 50/50 to be worth $200 or $0. It is also fairly priced if there’s a 20% chance of it going to $500 and an 80% chance of $0.

There’s this vocal VC named Keith Rabois who aggressively cheerleads his companies. I don’t know the guy. His online persona exudes many standard deviations of F-U confidence. Sounds par for the uber-rich these days, but he’s extra fun because he’s pugnacious. And got baited into a silly pride bet.

Here’s a tweet from investor @compound248:

We wouldn’t talk about this in the Masochists section because this is fairly basic financial reasoning. The type that really needs to obvious to everyone in a society is flirting with a simulcrum of the movie Rat Race. But it’s appropriate to spell out the opportunity here in gambling terms.

Keith is offering an even-money bet, his $100k to Compound248’s $100k on the stock multiplying by 31.5

If you think in odds:

Keith is offering even money on a 30.5-1 odds proposition

That might be more clear when you think of Keith buying the stock. If he buys $OPEN he risks losing the stock price or 1 bet and if the stock goes up 31.5x he wins 30.5 (because the 1 bet or amount of cash he spent for the stock is not part of his win or return).

It’s similar to how a stock 2x’ing is 100% return, or 10x’ing is a 900% return. A stock that 10x’s paid 9-1. You risked S, you won 9S if S is the stock price.

Normally when you buy a stock, you get paid dollar for dollar as it moves times the number of shares you have. If the stock doubles you make S in profits which is how much you risked when you bought it. You are paid in proportion to the move.

Keith needs a heroic move to simply get paid even money. His proposition is an arbitrageable violation of how return works. I don’t know anything about Compound248’s outlook on $OPEN by him taking the bet. He could be bullish or bearish. When you hear the proposition, your mind shouldn’t go to “Is $OPEN a good or bad investment?” because what you should do doesn’t depend on this assessment.

Keith’s offer is free money regardless of your outlook.

He’s laying 30.5-1 odds where the max loss is $100k.

So you solve for “How much OPEN do I need to buy to make a $100k profit if it pays 30.5-1?”

It’s simply:

1/odds * bet size

1/30.5 * $100k = $3,280.21

I need to buy $3,280.21 worth of shares. Since the stock was $8.48 that’s just about 387 shares.

If the stock goes to 0, you lose the $3,280.21, but Keith hopefully pays $100k. If the stock does go up 31.5x, you break even.

You could also structure the hedge so that at a stock price of 0, you break even. You buy $100,000/$8.48 or about 11,792 shares. If the stock hits Keith’s bogey you get paid 30.5 on your $100k and you happily peel off 1 bet size to him as a tip. Any share quantity you buy between 387 and 11,792 is a guaranteed win.

An amusing post-script to this story is HF manager Benn Eifert requesting $10mm of action on this proposition. Of course, Keith said no — he’s confident not stupid. Keith said he did the bet with Compound248 just to shut the “troll” up or something.

I don’t understand how rewarding a troll with the easiest money I’ve ever seen is anything but encouraging future trolls, but maybe this is why Keith is rich and I’m writing on the weekend.


Money Angle For Masochists

Tomorrow, we are going to launch the annual Black Friday/Cyber Monday discount for moontower.ai. It’s the only sale we offer during the year (current subscribers will be able to extend at the discounted price as well).

The app’s selling point, what makes it different, is its “point of view” on vol. It really starts from “what’s normal in the options market now” vs what sticks out. The analytics are geared towards answering that question because that’s how you find contradiction.

If sunscreen and umbrellas are simultaneously expensive, it might be because there’s a sunshower expected — but do the odds make sense? Before you could even reason about that you needed to know that sunscreen and umbrellas were both expensive in the first place, otherwise you wouldn’t even consider the question. Questions are where opportunities live.

The price of options is summarized by properties of vol surfaces, which in turn, can be compared to each other. We do the measuring and comparing to point out where the questions are. Options are not as simple as point spreads. Strikes themselves are fixed but the stock price changes, time passes. That same contract’s properties morph like natural landscape seen through a time-lapse camera. We are your guide in this wilderness.

We surface what types of trades look relatively attractive from the vol trader’s vantage point. You can think of that as a solid hypothesis based on the data, but from there, you can adjust based on your knowledge or opinion of what is going on in the name.

We don’t make guesses about the future. We don’t say do X and you will make money. It’s obvious to anyone who has ever taken risk that handicapping the future is not enough to make money. Think about it. How confident are you that the current price of SPY is not the all-time high? Probably 100% and rightfully so. The “SPY to be up 1 cent” one-touch option would be priced at 99.99999% percent. The knowledge is replacement-level not value-add.

You don’t sign up for Bloomberg because it tells you how to make money. You sign up because it helps you see*. And seeing in the correct terms is a prerequisite to profitable decisions. It’s the base of the pyramid upon which you layer the rest of your process.

That’s what we’re solving for in the options niche. The vol trader’s lens.

I made these vids this past week to offer a concise description of some of the key tools for seeing like an option trader:

*When you sign up for analytics, you usually do so knowing what you want to see. But also, there’s a built-in education. You learn what matters to others as well. Digital real estate is not scarce but deciding how to fill it is still constrained by taste and demand. The option pricing software that I used in market-making was also full of clues about best practices because professional users drove the features. What’s interesting when you have an analytics product that serves both retail and enterprise is the features can be a weaker signal about what matters. B-to-B vs B-to-C.

Stay groovy

☮️

Moontower Weekly Recap

Posts:

Moontower #292

Friends,

I really liked this listicle by Sasha Chapin:

50 things I know

I was gonna do my usual thing of sharing which items from the 50 resonate most for me.

I’ll give you one.

11. I know that talent doesn’t feel like you’re amazing. It feels like the difficulties that trouble others are mysteriously absent in your case. Don’t ask yourself where your true gifts lie. Ask what other people seem weirdly bad at.

But what I want to know is which of these land for YOU.

This was an excuse to do a project.

Here it is…go vote:

https://sasha.moontowermeta.com/

I have been doing a lot more vibe-coding recently. This project was an excuse to make something that required a database backend to record the likes and user sessions.

I used AI to then document the process which you can read about here:

General environment and stack:

👨🏽💻Setting up Git + Vercel + Terragon

Specific for the sasha voting page:

1-page guide

🔍Detailed tutorial

You can find a new portal here and in my signature down below:

🤖Resources to Get More Out of AI

Related and timely — this week Khe documented making a CRM which is the next-level up because it uses authentication (ie username/password to login):

I coded an entire CRM from scratch

If there are any resources you love as you explore, feel free to share!


Money Angle

Essential Wisdom from Twenty Personal Investing Classics (6 min read)

Elm Wealth distills investing lessons from 20 classics, cross-referencing them with James J. Choi’s paper Popular Personal Financial Advice versus the Professors (Journal of Economic Perspectives, Vol. 36 No. 4) that analyzed advice across 50 best-selling personal-finance books, revealing where popular wisdom aligns (or clashes!) with financial theory.

This stood out to me:

Bear in mind that the first twelve books listed above are written for the broad audience of all investors in developed market economies, with particular focus on US investors. It is well-known (and disturbing) that the financial literacy of this audience is, on average, quite low – as evidenced by a mean score of 56% (yes, that would be an “F” if not graded on a curve) on the below five-question quiz, known as the “Big Five” test by researchers. A survey conducted in 2021 found that less than one third of respondents answered at least four of them correctly, the threshold researchers define as “high financial literacy.” At least as concerning as the low test scores is the fact that the scores themselves have fallen dramatically between 2009 and 2021. If you decide to read some of these books, don’t be surprised to find a good deal of the advice proffered seems blindingly obvious if you come to them with above-average financial sophistication.

Umm, the quiz:

Article content

With the growing zoo of money distractions (crypto, gambling, prediction markets) and the results on that quiz, I’m guessing a large swath of society is gonna feel like there’s a financial tapeworm in their wallets.

I tweeted this a few days ago:

Article content

Let’s focus on evergreen financial hygeine. These were common themes I saw in the books Elm Wealth selected:

  • Diversify. It’s the rare free lunch: combine two assets with equal expected return and volatility, and your portfolio’s risk-reward improves.
  • Minimize frictions. Avoid fees, taxes, and excessive trading.
  • Reduce touchpoints. The fewer chances to act on emotion, the better your long-term results

Just to piggyback on the diversification bit. It sounds trite, but you’ll hear some people push back against it with the buzzword “deworsification”. When you’re as smart as Warren Buffett maybe you can use this word. But Buffet himself recognized Ed Thorp was a genius despite Thorp’s strong conviction in diversification. [And vice versa, by the way. Thorp’s recollection of hanging out with Buffet when they met in their 30s is pretty heart-warming. Game recognizing game. Apparently, after dinner Buffet showed Thorp a toy he really liked — non-transitive dice. Think of them like roshambo. A beats B which beats C which beats A.]

Here’s the cold-ass truth. Not diversifying is incinerating money. Looking back at your concentrated outcome and saying “see” is not proof of anything but survivorship. In fact, you can prove mathematically that diversifying is a free lunch.

What would you rather own?

Portfolio A: a single stock with an expected return of 10% and 30% vol

OR

Portfolio B: an equal-weight portfolio of 2 stocks where each has 10% expected return and 30% vol but are 70% correlated

💡Stuff you can read if this is not clear:

The proof is sitting there in market prices too. A diversified portfolio of inferior credits will have a higher rating than the bonds in the basket. A higher rating means a higher price (lower yield).

The nuances of that are better understood today than they were in the heyday of CDO-squared.

🔗See the GFC through a quant’s eyes

Of course, diversification always means you left something on the table in hindsight. You sign up for FOMO. But this is the nature of every decision. If you get crushed, you wished you traded zero and if you win, you wish you traded more. Results alone tell you nothing about the quality of your shot.

To complete the point:

“If you invest and don’t diversify, you’re literally throwing out money,” stated Jeff Yass. “People don’t realize that diversification is beneficial even if it reduces your return.”

Why is this the case? “Because it reduces your risk even more,” added Yass. “Therefore, if you diversify and then use margin to increase your leverage to a risk level equivalent to that of a nondiversified position, your return will probably be greater.”

The modern pod shops are another triumph of diversification, which takes us to the next section…


Money Angle For Masochists

I am impressed by the multi-managers on the whole. They continue to generate positive returns with outstanding Sharpe ratios and thus far don’t capture the same downside as conventional 60/40 portfolios.

I think of them as the holy grail marriage of deep security research that you would have associated with a long/short fundamental manager plus the quantitative risk management and attribution metis that prop trading firms trading their own money have accumulated through the decades.

Many investors, usually from the cheap seats, want to hate on them because they don’t match the SP500 plus their pass-through fees are multiples of typical fees. Not to mention, hedge fund managers are just natural villains to normal people who maintain a Richard Scarry worldview about which jobs are valuable (eh, like any competitive profession, some of them are decent and some of them are vampires).

Regardless, this quote from Byrne Hobart conveyed something I never found the words for, so as soon as I read it, I had to clip it.

From Why Does Volatility Matter?:

If the portfolio you’re looking at is 100% net long conventional asset classes, and if you think it’s absurd to pay high fees in order to match the S&P with less liquidity—lucky you! You’re part of society’s financial shock absorber, a middle class or above saver in a rich country with functioning capital markets. But if you’re in that position, there’s a very real sense in which joking about how the S&P has outperformed complicated multi-manager setups year-to-date is a form of financial punching-down. They have a different benchmark, and a harder job. And they’re doing you the very generous service of ensuring that the next time you buy the S&P 500, the price of every single component reflects the collective attempt by thousands of professionals with massive data and analytics budgets who are all trying to push the price 1% closer to optimal.


I want to share another post from Andrew who I introduced last week.

So-Called “Bonds” in Prediction Markets

Great subtitle:

Rare events teach slowly

Stay groovy

☮️

Moontower Weekly Recap

Posts:

Moontower #291

Friends,

The phrase “studies show…” is almost always followed by bs. To understand why, I’ll point you to a post by David Epstein.

David is the author of RangeThe Sports Gene, and the new book Range Adapted for Young Readers which I bought for my 12-year-old son and nephew.

I’ve been a long-time reader of David’s letter and this post is both useful and timeless.

Everything in Your Fridge Causes and Prevents Cancer

It’s a reminder that outlier studies and results in general make headlines, but are statistically inevitable if you do enough studies.

Excerpt:

It wasn’t every sauna enthusiast who reaped the supposed protective effect against dementia; it was specifically those who used a sauna 9-12 times a month. Sauna bathers who hit the wooden bench 5-8 times a month — sorry, no effect. And those who went more than 12 times a month — again, no luck.

That should raise a caution flag in your head.

When only a very specific subpopulation in a study experiences a benefit, it may indeed be that there is some extremely nuanced sweet spot. But it is more likely that the researchers collected a lot of data, which in turn allowed them to analyze many different correlations between sauna use and dementia; the more different analyses they can do, the more likely some of those analyses will generate false positives, just by statistical chance. And then, of course, those titillating positive results are the ones that end up at the top of the paper, and in the press release.

Here’s the point I want to hammer home: when you see a tantalizing health headline — like that saunas prevent dementia — keep an eye out for indications that the effect only applies to specific subgroups of the study population. Even if the headline is very authoritative, revealing nuggets are often buried lower in the story.

I want to stress that you shouldn’t assume the sauna results can’t possibly be true. But when you see Bears-undefeated-in-alternate-jerseys type conclusions — and someone is claiming one thing causes the other — you should hold out for more evidence.

This doesn’t just happen in health news. Investing/trading is another area where making a mountain out of a statistical molehill is rampant. Unless you are specifically studying a phenomenon that you’d expect to be discontinuous (binary, “phase change”, threshold cutoff) you should be wary of any signal from a specific range of an otherwise continuous function.

I’ll take a simple example from Kris Longmore’s article explaining how month-end rebalance trades work. The post is titled How Wealth Managers Pay You To Trade. He writes (emphasis mine):

How I’d Test This

So here’s the hypothesis: if we can identify which asset outperformed during the first part of the month, the underperformer should outperform as we approach month-end, when rebalancing pressure is likely to be greatest.

The first step is simple. Pull daily data for SPY and TLT going back as far as you can get it (I used data from 2007). You can get this from Yahoo Finance – nothing fancy.

Then ask a straightforward question: If I know which asset outperformed during the first 15 trading days of the month, can I predict which will outperform during the last ~7 trading days?

Why 15 days? Because it’s roughly two-thirds of a trading month, and it gives us a reasonable window to identify the outperformer before month-end rebalancing kicks in.

Could you use 10 days? 20 days? Sure. But 15 seemed reasonable and shouldn’t really matter much. If it did, then that would be a big red flag. We want stuff that’s fairly robust to the actual implementation details.

Back in my floor days my biz partner was incubating a futures trend strategy and he’d have me look at the backtest results. I’m no scientist, but I knew enough to realize that if the signal depended on a particular value of the parameter (ie the exact amount of what defined a “breakout”, the number of lookback days, etc), then the result was overfit.

It’s the same idea as David’s sauna therapy study.

When you are in a competitive domain where many people are constantly mining, “too good to be true” discoveries should be met with extra skepticism.

A current example of this is the so-called Mississippi Miracle in which both the left and right appear to have an axe regarding the childhood literacy improvement in Mississippi schools. It checks the box of “domain where many people are constantly mining” so interventions that show huge returns deserve a lot of skepticism. You can count on Freddie deBoer to deliver that, but I think the pushback in the comments section of his post show the complexity:

There Are No Miracles in Education

 

Would be interesting if there was a prediction market on how much literacy scores would improve in places that decide to adopt the Mississippi approach?

Which brings us to this week’s Money Angle, which should get a rise out of you…


Money Angle

Prediction markets are all the rage. They even played a main character role in an episode of South Park just a few weeks ago with Kalshi being specifically shouted:

 

On Friday I shared a rare interview with SIG founder Jeff Yass that came out this week about prediction markets:

Spooky? Jeff Yass on Prediction Markets

Spooky? Jeff Yass on Prediction Markets

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Oct 31

 

On the subject of prediction markets, long-time Moontower sub Andrew Courtney has launched a substack with many of his recent topics being analysis of prediction markets. His thought processes look familiar because…well, Andrew retired quite young being an extremely successful SIG trader himself.

You can get started with these posts:

🔗from the Kalshinomics Lab: conditional election probabilities

🔗are you good or just up?

🔗Relearning Math at 38 — Andrew was at the top of the Math Academy leaderboard for a bit which iirc corresponds to learning math with the same time commitment as a full-time job. My kids and I have looked at the top of the list thinking “who the heck are these people?!”. I was envisioning autistic homeschooled kid not retired SIG trader.

Finally, this is also Andrew’s site:

Kalshinomics

If you are in the Philly area, he’s done meetups for prediction market enthusiasts.

Fun fact: I told Andrew I was going to boost his awesome letter this week and I asked him to make me a market on how many subs it would lead to.

He gave me a 90% confidence interval which I thought was a good market although too wide to trade on. I showed him a 175 bid if he wants to hedge his happiness. We’ll see what happens.

Good handicapping practice would be to try to list the info you’d like to have in making such a market!


Money Angle For Masochists

The “Masochists” header word this week is a pointer to “aspiring traders”.

I’m going to reprint Joel Rubano’s tweet in full. Joel is a friend, energy trader, author and entrepreneur running a corporate trading education company with a focus on commodity trading and hedging.

His book: Trader Construction Kit

The tweet pairs well with the post from last week’s so you’re interested in trading.

Joel:

I had the opportunity to guest lecture to a university class yesterday and got some questions about resources for students interested in working toward a trading seat.

The good news is that there are massively more and better resources available now than ever before. The bad news is that for every useful book, class, or podcast, there are 999 more that are worthless at best and massive value destructors at worst.

A few hints to help sort the wheat from the chaff:

Anything that tells you trading is easy is lying to you. Trading is a brutally hard game played against literally the smartest, most disciplined, most aggressive people in the world. The people who survive and thrive tend to welcome that specific challenge, even though most would not describe their time on the desk as “fun.”

Anything that claims a risk-free or can’t-lose strategy is garbage. Most professional traders are hoping to be right 50–55% of the time and relying on extremely strict discipline and risk management to be profitable with that hit rate. They also have to manage capital so they can survive stretches of worse-than-normal performance, which invariably happen.

Anything that tries to sell you trading as a lifestyle — the cars, the watches, the vacations — is almost certainly a scam. Real traders are not sitting there thinking about what the money buys in real time; that’s distracting and leads to bad decisions. There’s even a famous passage in Reminiscences of a Stock Operator about a group of traders who all try to make enough money to buy a fur coat, and they all fail because they were focused on the coat instead of on playing the game well.

Anything that says “anyone can do it” ignores how markets actually work. Most markets are zero-sum: people have to lose for other people to win. The softer version — that anyone can become a trader if they just grind — is also not really true. The job demands unusually high levels of discipline, curiosity, intellectual honesty, and competitiveness. Some people have those traits and can develop into professional traders; most people don’t, and that’s fine. The good news is that there are lots of trading-adjacent roles (risk, research, sales, tech, execution, ops, product) that let you work on markets, think about markets, and have a productive, interesting career without being the person taking risk.

Anyone promising something “just like what the pros use” or “better than the professionals” does not understand what professionals actually have. Elite hedge funds, banks, and merchant trading firms spend huge amounts of money on proprietary tools, data, infrastructure, and staffing to compete in an intellectual arms race. A single trader can easily consume hundreds of thousands to millions of dollars’ worth of technology and information resources per year, which is one reason their profit targets are so high. You are not getting that for $29.99 a month.

Anything that claims “the edge is AI” with no further detail is almost certainly not going to outperform anything. Yes, serious trading firms are racing to integrate AI, and yes, AI will be useful for specific tasks. But AI is very good at some things and still not very good at others. If someone is just putting a thin interface on top of a generic stock-picking model and calling that “AI-driven alpha,” it’s not only unlikely to be useful — even if it does work for a bit, it will almost certainly get out-competed by more specialized, internally developed tooling at a bank or hedge fund.

Ultimately, if you’re serious and you’re early, your main job is not to find a shortcut; it’s to build the traits that compound: discipline, honesty with yourself, curiosity, and competitiveness under stress.

 

Stay groovy

☮️

Moontower Weekly Recap

Posts:

Moontower #290

Friends,

Let’s hop right into a recommendation.

This essay is packed with useful decision frames. If you’ve been with me for awhile I think you’ll understand why I’d appreciate it.

In praise of quitting (Cate Hall)

From the opening:

  • the danger is in devoting our days to something that fundamentally doesn’t matter to us, because we’re too afraid to cut our losses.
  • Tournament poker is basically about finding the highest-value uses of a scarce resource, your chips. The fact that losing those chips means getting completely locked out of a shot to win major money means that their opportunity cost is high. This means it can be a big mistake to commit yourself to hands that are somewhat positive-value in expectation, if you have good reason to believe there will be better, higher-value opportunities…Life is, of course, just like this: You get only one shot, and it’s up to you to make the most of it by rejecting okay or even pretty good ways to allocate your time or other resources — to hunt down the opportunities to make really great bets on yourself. Do not make barely positive-value bets with your life!

A description of almost anyone can relate to by middle-age, if not earlier:

The interesting thing about steady jobs is that they’re actually not so steady. They are static in a conceptual sense — in the sense that if you say you’re a “lawyer” when you’re 30, and say you’re a “lawyer” when you’re 50, there is the same label for what you do. And that can feel like steadiness, like a reassuring kind of coherence to your life story.

But the truth is that everything is in constant flux. Beneath the labels, life continues evolving all the time. Your interests change, companies change, and industries change. Given that your “steady job” is constantly evolving, even if you picked the highest-leverage option initially, there is a low chance that it will remain your highest-leverage option over time.

The same goes for places to live, relationships, opinions, and hobbies. Over time, these things can degrade in value or resonance — and yet still retain the emotional pull of their initial promise. And when this happens, people often stay too long.

Cate offers some exercises or what I think of as useful frames:

By default, we tend to think of “choices” as the kinds of things that take us off the path we’re already on. From this stance, it doesn’t feel like we are “choosing” to go to our job every day, or choosing to remain where we live. The scary thing is that this means we can actually be making the biggest mistake of our lives on a daily basis, despite it feeling like nothing is happening at all. If we want to evaluate whether our current set of choices is really best or whether it’s just inertia keeping us where we are, it can be powerful to upend that frame.

Try it. Go around your day, narrating all of your choices to yourself. With everything you do, consciously say, in your head: “I am choosing to do this, because it’s the best course of action according to all the information I have available.” See if it feels true. It might — perhaps this exercise will reinforce your conviction. But you might also find that entire regions of your life suddenly look strange. The declaration that you’re doing the best thing will sound like hollow propaganda, an attempt to convince yourself of something you know just isn’t so.

More:

Another powerful exercise, of a similar kind: Imagine that you were instantly unsubscribed from everything in your life. All of your choices undone — where you live, who you’re with, what you do with your time. All of a sudden, you’re a completely empty canvas. And then, imagine that you have the power to bring back each element just by hitting a “resubscribe” button, like it’s an email newsletter. Being honest with yourself, which elements would you hit “resubscribe” on?

Once you realize you’re choosing something, you regain the ability to un-choose it.

Note that un-choosing doesn’t always mean quitting in the complete, traditional sense. It might just mean an alteration — working hard to establish a new phase in your relationship, or changing roles at your job, or moving to a different neighborhood rather than a different country. This, too, is strategic quitting: declaring that a given battle is over so that you can win the war.

She closes with a bright side.

Leaving can still break your heart even though it’s the right thing to do…But something to remember is that there is always some unknown part of the future that you will be equally fond of.

When people think about quitting, it’s hard because they’re comparing the rich web of attachments they have now to some mostly blank slate, or, worse, the possibility of disaster. However, what’s more realistic to imagine, if you’re leaving something you’re no longer aligned with, is a future with more to love than you have now.


My 2 cents since we’re here.

Quitting the familiar always feels risky. And to be clear, it often is. But it’s also risky to stay and even though we can feel that in our hearts, we don’t seem to warn people about that risk with the same urgency we do about when they plan to change.

The asymmetry is an expensive risk reversal. Paying up for the put, and hittin’ bids on calls. Playing for upside, I don’t mean financially, although that can be included, demands courage. Not heroism. Small courageous steps. Folding a comfortable hand never feels heroic, but it does take courage. It risks looking like a fool.

We are surrounded by grand examples of ambition. Bottomless appetites for wealth and power. But figuring out how to live on your terms, around people you are happy to be around, working on things that light you up, and staying true to your values is an ambitious goal. Pulling that off is hard because unless you got lucky and ended up on YOUR path from the start, at some point you will need to know when to quit.

I don’t know where I heard it, but someone said the reason some finance people stay in finance (unhappily) long past satisfying their financial goals is that they can’t do anything else. Not in a “they lack the ability” but in a learned helplessness kind of way. They cannot stomach the hit to their identity, status, or sense of usefulness, even if all of it is in vain. For appearance. For others. For lack of creativity. Soul last seen on the back of milk carton at age 17.

On a personal note, even having went through a substantial quit, I’m still not here to glorify it. I effectively run a craft consumer-facing small business between the writing, consults and option analytics. Bruh, I’m teetering on the edge of self-doubt and self-belief from day to day.

Making money and creating surplus go together. That I make less than I used to hurts because it feels like a statement about the surplus I create.

[I obviously understand that it’s not that simple. Leverage and ability to capture a share of surplus are giant inputs into what you actually get paid. That there’s no-name closet indexers richer than your favorite drummer is capitalism’s bunion but I’m not suggesting we amputate the foot even if I’d get some perverse joy from clawbacks against people who suck.]

Still, I wrestle with this quite a bit. I don’t really see myself as a businessman. As someone who would spin something up just because they see an opportunity. I’ve always been impressed by those kinds of people because I wish I could be like that. But it’s hard for me to care about something unless I love it. I don’t care about solving a problem just because it exists. There are infinite problems and I have one attention span. To a businessman, profit helps them filter. But more money than I actually need* is not motivating enough to do work I don’t care about. How would I even be excellent at something I didn’t care about?

But this perspective is a constraint of my own making. I don’t get to eschew opportunism and then complain that’s how the world and economy work. As it goes, I’m trying to figure out how to make more money doing these things that intersect my interest and ability. There’s a better product-market fit at the end of this rainbow, but finding it is harder than trading, and there’s no guarantee it will pay as well. But I’m immersed in the process of going there. And for that feeling, quitting was right for me.

*Adulting means you gotta do whatever you gotta do to make what you need OR lower what you need. But I’m talking about the same decisions we all make on the scale that is personally relevant. For some, it’s the choice of doing X for the 100k they need or Y for the extra 50k, and for others it might be the choice of $500k working remote or $1mm being on the road 60% of the time. Cate’s point in this essay is that everything is a choice and when you forget that become an entitled victim. Or to use one of my favorite lines…you’ve exchanged a walk-on part in the war for the lead role in a cage.


Money Angle

I want to clarify a statement from my chat with John from Risk of Ruin.

I said “vol trading is easier than directional trading”.

This is something I’ve felt from experience. I long attributed it to derivatives pricing being, well, derivative of an underlying. Trading an ETF or index future, both derivatives, is “easier” in the sense that there is a fair value with respect to some assumptions like cost of carry but the variation in the assumptions is vanishingly small compared to the error bars on the assumptions one makes when formulating an opinion about a stock price.

For options, most of the inputs except volatility also have error bars that are far smaller than anything you’ll assume about a stock.

Which brings me to volatility.

Volatility is more stable than returns.* This is why quants target risk in their sizing, not returns.

🔗See Know-Nothing Sizing for a fuller discussion. It’s an idea that underpins my approach to investing and risk management.

So if handicapping volatility is easier than handicapping returns, shouldn’t everyone just trade options for that sweet, easy cash?

The fact that it’s easier, also means the competition is fierce. It’s a zero-sum, capacity-constrained game. Predicting vol is easier than predicting returns, but…so what? You care about “how easy is it to make money?” and that is not easier.

The distinction reminds of this Daryl Morey bit on sport analytics:

Our underlying data is more predictive, quite a bit predictive. I talk to a lot of quants on Wall Street, and I tell them our signal to noise ratio using whatever measure you want….And they go like —whoa, you guys are — that’s incredible. And I’m like, yes, but you remember, we have to be best of 30. You guys just have to beat the S&P by 2% and you are geniuses. So each industry has its own challenges.

*For the option enjoyyyyers who are thinking “Bruh, VVIX is way higher than VIX, how can you say vol is less volatile than the vol of returns?”, here’s my rebuttal: What’s your 90% confidence interval on SP500 returns next year vs SP500 1-year realized vol?

An investor doesn’t care about vol of vol as if they are trying to price an option on VIX. If SPY realizes 14% give or take 5 points for a year (this is about the high/low range of 365 day vol using overlapping data for the past 4 years), this is not as destabilizing as the outright returns being say -5% vs +15% which is probably an even narrower relative range than 9% to 19% for a 1-year realized vol.

Money Angle For Masochists

Speaking of VIX…

Here’s an FYI that reinforces a lot of moontower 2025 writing on option synthetic futures.

This is from my IBKR screens from 10/22:

Spot VIX was 18.4

I highlighted the March VIX future. It had a mid-market of 21.725

The ATM strike for options on VIX expiring in March is 22.

The combo or price of the 22 synthetic =

call price – put price = 3.50 – 3.78 = -.28

Synthetic future = Strike + Combo = 22 -.28 = 21.72

No arbitrage available folks (as expected).

The synthetic future on VIX and the actual VIX futures trade in line.

💡The VIX options typically expire on the Wednesday morning preceding monthly option expiry cycles. The future expires on Thursday morning, 1 day later. For them to trade out of line with one another would imply a significant jump in forward vol for 1 day, and working through that math with our forward vol calculator can be educational. Unless there is an extremely impactful event on that Wednesday, I’d expect the actual and synthetic futures to trade in lockstep. A good homework for option firm trainees might be to draw indifference curves for various DTE (ie 5, 10, 30, 60, 90) of forward vols based on the VIX future vs synthetic future. I haven’t done it, but I imagine it will be self-evident that any variations between the 2 would be worth trading against, justifying why they trade in lockstep.

Like I said I haven’t done this, so I’m going off intuition on how forward vol works. If you are a VIX complex arb trader (I know you’re out there) feel free to correct me.

 

Stay groovy

☮️

Moontower Weekly Recap

Posts:

Moontower #289

Friends,

Last Sunday morning’s letter talked about reading. The night before at my cousin’s wedding, he quoted CS Lewis in his speech. Later that Sunday, he was hosting a post-wedding fiesta at his house and the topic turned to book suggestions.

He recommended Lewis’ Screwtape Letters. I have the book but haven’t read it.

[Actually we have 2 copies now because my wife ordered it on my cousin’s rec not knowing I had it, but it works out since I can’t find mine since the move.]

My mother was visiting this week for the festivities so she opened it up and read the first page. She couldn’t understand it. I took a peek. I could read it just fine and in fact I quite like the style but it’s certainly harder than reading popular novels. My mother is a voracious reader, both fiction and self-help, but it’s all Dan Brown level.

I looked up its Lexile Score*.

*According to the Gemini blurb at the top of your Google search that steals views from someone else’s site, a lexile score is a measure of how difficult a text is based on attributes like sentence length and vocabulary

1170.

I looked up Lexile scores for Harry Potter or Dan Brown stuff. It’s all in the 850-920 range.

For context, I highlighted those mid to upper 800s here:

A top decile 3rd grader reads the same as a bottom decile 9th grader. Popular writing is about 4th-grade level. I asked my 7th grader to read a page from Screwtape and he liked it! He started it this past Thursday, after wrapping the Unwanted series he was addicted to. I looked them up. Only about 800 Lexile. Confirming my frustration that while he reads a ton, it all seems below grade level.

But I guess that’s true for almost everyone.

If interested, years ago, I compiled this table of books for kids based on reader recs or personal experience. It includes Lexile scores:

https://notion.moontowermeta.com/book-ideas-for-kids

 


Job Posting

Financial Sourcer/Researcher – Part-Time, Remote (Greythorne Associates)

We’re looking for a skilled researcher who can find talented quant traders, PMs, and strategists—the people who don’t respond to generic recruiter messages.

Greythorne is Stacey Crognale’s recruiting firm. Stacey was the director of HR at SIG when I was hired back in 2000. She started Greythorne in 2007 and specializes in quant finance with an especially strong pipeline in prop trading. This role is not an external mandate, but to work with her directly.

—> Apply here


A chat with John Reeder

John is the man behind the Risk of Ruin podcast. He interviews advantage gamblers and the occasional investor. The format is one of my favorite. It’s more like an audio essay than an interview. He does a lot of writing for them, weaving together his knowledge and lessons from experience and discussions, and then treats the guests answers the way you quote in an essay.

I’ve always been impressed by how well they are put together not to mention how much work they clearly require. As a long-time fan, I was totally honored to be invited on. John’s questions are always thoughtful and unique.

🎙️The episode is available on Spotify

We don’t get into the nitty gritty of options because that’s not the audience here, but for those interested in options, I do explain why vol trading is easier than directional trading (and why this is not the refuge it sounds like).

 


Money Angle

So You Want to Abolish Property Taxes ( Lars Doucet)

I remember being on some freeway, I mean highway, in the DFW area and seeing a billboard for some candidate promising to 86 property taxes. As a CA resident drawn to Georgist economic principles, in no small part due to Lars’ persuasive education, I’m just shaking my head as I whizz past the smarmy ad. Like what’s wrong with you? Your state’s economy is a positive role model — no state income tax, high property taxes, and allows builders to build. And you come up with this?

If your plea of “Don’t California My Texas” amounts to symbolic own-the-libs gestures like banning rainbow crosswalks and cannabis while inviting, hell, speedrunning Prop 13 distortions, then you are about as serious as a pixie stick.

Lars breaks it down so well, just check it out. If nothing else, read the section Answers to Various Objections.

 

Money Angle For Masochists

Option trader and author Euan Sinclair published a labor-of-love project that will become a cult classic for trading nerds.

The Theta Pig Letters

It is a remarkable pastiche of none other than — The Screwtape Letters.

The Screwtape Letters are an escalating correspondence between the devil and his demon protege Wormwood. The devil is teaching his dear nephew how to sabotage the lives of humans.

The Theta Pig Letters are an exchange between a master manipulator and his understudy whose trying to undermine traders attempts to succeed.

It’s not only brilliant, it’s fun to read. The condescending tone towards the incompetent nephew is relentlessly hilarious.

You can download it here:

The Theta Pig Letters
665KB ∙ PDF file

Download

A selection of excerpts:

  • The mistakes described here are not rare. They are routine. They do not announce themselves as errors. They arrive dressed as insight.
  • My dear Backtest: Congratulations on your first assignment. There is nothing quite so exhilarating as the early days of a Patient’s trading career, when vanity and vulnerability sit so invitingly close together. Trading, you must tell him, is uniquely stressful. Unbearably so. More grueling than any other occupation. (Do not, under any circumstances, allow him to reflect that bartenders suffer drunks, that teachers manage thirty howling infants, or that soldiers are expected to remain calm while being shot at.)Encourage him to think of himself as a kind of artist-warrior—misunderstood by ordinary mortals, ennobled by his suffering. His partner’s raised eyebrow becomes an attack on genius. Any well-meaning question is interpreted as doubt. He will learn to ignore those who do not mirror his self-image and surround himself only with those who validate it.And better still, he will eventually seek out “kindred spirits”—online forums, trading chatrooms, or overpriced mentorships—where the mythology is reinforced. He will not look for conflicting views or rigorous critique. He will look for comrades in suffering, not comrades in truth. A good trader seeks out disagreement; your Patient will seek only confirmation. the more he believes that trading is uniquely punishing, the less responsibility he will take for improving his own skills. The idea that competence, not courage, is the antidote to stress must never cross his mind. If he begins to study properly, to practice restraint, to track his errors with cold detachment—well, then you will have lost him. He will, without realizing it, become sturdy.
  • Let him convince himself that the law of large numbers is his ally, not his executioner.
  • Let them drown in a sea of partial differential equations and symbolic regressions.
  • Let them believe that beauty implies truth. Encourage him to chase symmetry where there is only noise, to assume continuity where there are jumps, and to impose causality where there is merely coincidence. Most importantly, let him believe that the clarity of a model matters more than its performance. That the elegance of his thinking is a substitute for testing. Make him allergic to heuristics. To approximations. To ugly truths. Let him scoff at simplicity and worship coherence. If you succeed, he will spend months—perhaps even years—building intellectual castles in the sand. He will conflate sophistication with strength. And when the tide inevitably washes those castles away, he will rebuild them: higher, more intricate, but equally unstable.Let him mistake thought for progress. That has always been our favorite kind of failure. And, Satan knows, you should be familiar with failure.
  • Let him believe that by reading financial statements, scanning headlines, and pondering macroeconomic conditions, he can infer what the market has missed. Encourage him to imagine that he is not reacting to price, but interpreting value. He will feel sophisticated. He will say things like “market overreaction” and “long-term thesis.” He will call himself a contrarian and imagine that patience is a strategy. Do not let him suspect that he is merely doing what everyone else is doing: consuming public information and projecting his own beliefs onto it. He must never consider the possibility that the balance sheet he’s analyzing, the CEO he’s quoting, the trend he’s spotting—are already priced in. Let him imagine that the edge lies in how he reads the data, not in whether that data is actionable.This is especially potent for Patients who fancy themselves worldly. They will cite books, articles, and podcasts. They will draw connections between oil prices and grain futures, between central bank policy and auto sales. Let them draw. Let them weave vast, fragile webs of inference and call it research.Most important of all, convince him that the more connections he sees, the smarter he is. He will not realize that each new variable adds noise, not clarity. You must never let him notice that it is merely confusion with a vocabulary.And let him pride himself on general knowledge. He has read The Economist, after all. He remembers something about China’s shadow banking system. He once mansplained negative interest rates to a bored babysitter. He will come to believe that markets reward this sort of cleverness. That his perspective is not just informed—it is rare.Do not let him test this belief. Do not let him look at the returns of those who trade on earnings reports or macro forecasts. Do not let him study the failure rates of discretionary portfolio managers. Above all, do not let him ask how many successful traders he knows who rely on reading. (Kris: profound…success is being repetitive, in some ways dull. A hammer. Types that fancy themselves intellectual is not the archetype anymore than you expect a professional poker player sitting in a chair 16 hours a day in poorly ventilated, unglamorous room with smelly dreamers to have a James Bond passport and home library.
  • Now we come to one of the most elegant diversions in our entire arsenal: the myth that risk management is the edge….If he were astute, he might see the absurdity of it all: that if risk management alone were the edge, then he could play the lottery with good position sizing and come out ahead. That perfect risk control, taken to its logical conclusion, simply means taking no risk at all. And there’s no edge in abstention.But he won’t see it—not if we play our part. Keep his thoughts on risk superficial. Let him use “asymmetric payoff” as a shield against deeper inquiry. Let him feel clever for “limiting downside while keeping upside open.” Just make sure he never notices that he doesn’t know where the upside is coming from.He will think himself disciplined. He will think himself wise. And best of all, he will think that not losing money is the same as making it.Let him worship at that altar, Backtest. It is a quiet church, and its congregation rarely asks for proof
  • Letter XI: But if he asks, “Why is VVIX diverging from VIX?” or “Why is NASDAQ volatility rising while the Dow’s is falling?”—that’s dangerous. Because relationships are where inefficiencies hide.How does skew behave as realized volatility rises? How long does it normally take for implied volatility to relax after a spike? Do the VIX options and SPX options account for the weekend in the same way? These are the sorts of wrinkles that arise not because the market is dumb, but because it is constrained. Because participants face capital charges, mandates, and rebalancing needs. The inefficiency is often the residue of friction.But if your Patient starts thinking in this way, we’re in trouble. He’ll begin to measure rather than guess. To observe rather than judge. To know the structure well enough to notice when it flexes. And that is edge.Stop this immediately.Distract him with headlines. Give him a guru who trades Tesla based on vibes and political bias. Feed him chart patterns shaped like ducks. Whatever it takes to keep him watching the show instead of reading the script.Snuff the curiosity. Leave him the confidence.
  • My regrettable aide,It seems I’ve overestimated you—again. You need help.You are enthusiastic, certainly. Eager. Occasionally—not often—effective. But in matters of craft, you remain a blunt instrument—loud where subtlety is required, impatient where patience would rot more deeply. And now, as the Patient begins to experiment with backtests, you must understand: this is a specialist domain that demands precision, not noise.Which is why I’m assigning you an expert.You will be working with Overfit. Do not speak unless spoken to. He does not tolerate enthusiasm. Or questions. Or you, if I’m honest— He will teach the Patient that systems must be tweaked, improved, optimized—until they hum with apparent perfection. He will praise him for reducing drawdowns, for raising Sharpe, for improving win rate by 0.03. And just when the Patient believes he has built something invincible… Overfit will let it collapse.Not immediately. That would be merciful. No, he will let it erode slowly, unpredictably, across market regimes that were never covered in-sample. And the Patient will blame volatility, not the process. He will tweak, not question. He will descend into an eternal loop of minor improvements. Like an old general planning for a war he fought many years previously.Overfit works in silence. In metrics. In elegance. He leaves no fingerprints—only code.Learn from him.He may even let you observe one of his routines: the 17-parameter breakout strategy that has a 1.47 Sharpe from 2008–2018, then disintegrates into noise. The Patient won’t discard it. He’ll “tune it for the new regime.” Again. And again. And again.Welcome to the second layer of hell, Backtest. You’ve played with belief. Now you’ll learn how to destroy through data
  • Letter XIII (Overfit’s first letter): Poison the foundation. We ruin the story in two ways: through data, and through method. The Patient must never suspect that his dataset is already betraying him. Some of the most reliable sabotages are achieved before the first line of code is written…
  • The point, Backtest, is not to mislead him directly. It is to cultivate his belief in rigor. To have him confuse exhaustiveness with validity, iteration with insight, and polish with truth.He must never think: “Does this idea make sense?”He must only think: “Can I make this idea work?”In this way, we will bury him in process. And the most beautiful part? When the strategy fails—as it must—he will blame himself. He will believe the system almost worked.That’s the mark of true failure: not that the backtest was flawed, but that it was nearly right.Almost correct. Endlessly refinable. Infinitely seductive.
  • Let Him Worship the Process. That is your final goal. Make him revere the ritual of validation more than the reality of outcomes. Let him define his identity as a “data scientist” rather than as a trader. Let him think that discipline replaces insight.He will become a guardian of statistical purity. A monk of withheld data. And he will lose money correctly. There is no cleaner form of failure than that.
  • Options. It is wonderful that the Patient has been allowed to discover options. Although I suspect you were just lucky in stumbling across this idea, it opens up many promising avenues for our project.You’ve done well to confuse him with the usual smoke: theta decay graphs, multi-leg jargon, and variations on iron condors named after insects. Now comes the ripest fruit: convincing him that an option strategy itself is an edge.Not the underlying market behavior. Not the statistical tendency of volatility to mean-revert, or of skew to overprice puts. No, no. The structure. The shape. The aesthetics of the trade. “My edge is in strike selection,” he said the other day. Selection! We are nearly there.Your task now is to seal the confusion between frequent and favorable. This is easier than it sounds. A wide short strangle, for example, wins often. Most days, nothing happens. The underlying chops around or drifts, the wings decay, and the trade is profitable. It is, in the short term, comfortingly correct. And like all good traps, it flatters his need to be proven right—again and again—until it suddenly doesn’t.What matters, of course, is the average outcome. Not the common one. But he has spent his whole life being rewarded for consistency, for pattern recognition, for turning in neat homework. The idea that a trade can win ninety times out of a hundred and still be a disaster is alien to him. Keep it that way
  • Your next task is to convince him that knowing the Greeks is the same as having an edge. We must not let him realize that the Greeks are merely descriptors—thermometers, not thermostats. They measure exposures, but say nothing of whether those exposures are favorable.
  • Make him identify as “a long vol trader” or “a short vol trader”. Make him pick a side before estimating which side is likely to win.
  • Whisper to him that true mastery lies in perfect delta hedging. That one day, with enough precision, he will out-calculate uncertainty itself
  • Your next task is to help him improve the strategy. Do not misunderstand me: we are not trying to make the strategy more profitable. We are trying to make it more elaborate.This is the art of post-discovery sabotage. The Patient has found something simple that works—some recurring pattern, some repeatable structure—and now feels the itch to “refine” it. Scratch that itch with gusto (it is no coincidence that mosquitos are on our side).Encourage him to add filters. Conditions. Weightings. Perhaps a volatility overlay. A moving average confirmation. A custom indicator. Or two. Or six. Suggest he look at volume, sentiment, cross-asset flows, macro overlays, news feeds. It doesn’t matter what. Just keep adding. Convince him that if he stops refining, he’s being lazy. That the real professionals are out there stress-testing their systems across twenty-seven regimes and fifty-three metrics and nine asset classes. Let him think elegance is amateurism. Most importantly, get him to optimize. Not once. Not simply. But obsessively. Every parameter must have a range. Every range must be backtested. Every backtest must have cross-validation. Let him run grid searches until his processor whines as much as you do. Let him discover the perfect lookback period, the ideal stop-loss, the optimal entry condition for a phenomenon that doesn’t. Over time, the original idea—the edge—will be so buried beneath rules and tweaks that even he won’t remember what made it work in the first place. If the strategy fails, he will have no idea why. He will re-optimize. Re-fit. Re-torture the data. Let the logic drown in complexity. Let the confidence die by a thousand knobs.
  • Automation: I am delighted that you have prompted the Patient to automate. This is the first real initiative you have shown and somewhat assuages my concerns about your ability and potential. Splendid. He will tell himself this is about efficiency. “The logic is sound,” he’ll say. “Why not let the machine handle it?” He will cite objectivity, discipline, and scalability. He will feel proud—professional, even. What he will not notice is that he is about to spend weeks automating a task that takes two minutes a day to do manually. This is the first victory: the gift of misallocated time. Every hour he spends writing code, debugging data feeds, and integrating APIs is an hour not spent thinking about the trade itself. He will be productive but only be producing something pointless.And the best part? Even if he gets it all working, it will still fail. Possibly not immediately, and probably not dramatically. But slowly, subtly, and in ways he won’t trace back to us.There will be bugs, of course. A mislabeled column, an off-by-one error, a missing data point that seeps through the system like a weeping pustule. He’ll fix these issues eventually. But each error will chip away at his trust. Not in the system—he’ll double down on that—but in his ability to implement it. He will begin to suspect he is the bottleneck. That more automation is the answer. Now comes the second level failure. Once automated, the trading process no longer asks anything of him. It runs. Quietly. Invisibly. His only feedback will be a daily P&L, eventually unnoticed, like the death of a woman who lives alone with the cats that will eat her. There will be no touch, no feel, no reason to monitor execution or slippage or spread. No sense of flow, timing, or friction. And because he no longer must think about the trade, he eventually won’t.The edge might remain, technically—but it will be unexamined, unmonitored, and unprotected. Execution costs will creep in. Fills will worsen. The strategy will degrade, not from a fundamental change in the market, but from neglect. And he will not notice.You must understand, Backtest: automation does not always kill by malfunction. It kills by abstraction. By replacing attention with convenience. By allowing the Patient to feel like he is trading when he is, in fact, only observing a spreadsheet. If you allow the patient to automate something out of necessity you will have committed a great error (and will be punished appropriately), but if he automates out of convenience then you have had quite a success. Please don’t ruin such a promising start.

 

Stay groovy

☮️

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Moontower #288

Friends,

My 12-year-old is a compulsive reader. To the point of me telling him, put the book down, go do stuff.

My 9-year-old has no interest in reading.

No bowl of porridge in this house is “just right” apparently.

I’m more alarmed by the 9-year-old of course. Our environment conspires against reading so it’s more important than ever to establish the habit early.

Warning: Old man yells at cloud moment

My niece goes to the local public school that is consistently in the top .50% of public high schools in the US. She had no summer reading assignment. She will be asked to read 3 books all school year.

Going into my freshman year of Christian Brothers Academy in NJ back in 1992, I was assigned 7 books to read over the summer. Every summer after that, we were assigned at least 4 books just for the summer. CBA is a good high school, but I live next to one here in CA and our local public school has a better reputation on academics. What if you don’t go to a top school? Or is this lack of reading some perverted thing that top schools do?

(My niece is taking AP Physics as a sophomore which used to be unheard of, so times have changed in good ways too. My niece’s favorite subjects are math and science and I’d like to think I had something to do with the math, given all the nerdom I’ve embarrassed my family with. What is not encouraging is discovering that there are only 4 girls out 40 students in AP Physics.)

Is standardized testing reflecting a reduction in standards or just the reality of dilution that you’d expect if a large majority of HS kids expect to go to college, as opposed to a few generations ago?

Some time back, I was in a conversation on Twitter about the SATs. Someone mentioned that the scores are inflated these days and you can’t compare across time. I didn’t realize that but sure enough one of my Twitter mutual follows chimed in. No other than Princeton Review founder Adam Robinson. He left a brief reply saying that while it’s complicated, it’s true.

Poking around online (a good place to start is the wiki for History of the SAT) you will find many calculators that allow you to compare SAT scores or at least percentiles between years. There have been many adjustments over the years, but the largest was the 1995 recentering. While my math score would be basically flat after adjustment my verbal was an 800 by today’s system. I haven’t delved into the decomposition of why verbal scores needed to be so inflated, but since the recentering occurred as early as 1995, it doesn’t make me think this is related to the decline of reading that has garnered more recent attention.

[To further muddy the waters, I’m not sure to what extent SAT verbal evaluation maps to any real-world acumen. I got a 790 on my SAT II – Writing, one of these subtests you needed to take back then, despite being a B student in English and literally walking out of a play at BAM in my late 20s because I was too stupid to understand it. My wife and I still think about how high-schoolers were laughing at Shakespeare’s jokes as we sat puzzled, trying to get cultured, only to give up by intermission. Yes, I write on the internet today, but it’s more like talking than the writing I saw in the classics I was forced to struggle through.]

This post by James Marriott suggests the decline is real. And why wouldn’t it be? Everyone sold 4 hours of their day to the biggest companies.

(Hey, at least your absentee ownership of cap-weighted indices investments benefit.)

The Dawn of the Post-Literate Society (James Marriott)

Select excerpts:

  • “To engage with the written word”, the media theorist Neil Postman wrote, “means to follow a line of thought, which requires considerable powers of classifying, inference-making and reasoning.”
  • In America, reading for pleasure has fallen by forty per cent in the last twenty years. In the UK, more than a third of adults say they have given up reading. The National Literacy Trust reports “shocking and dispiriting” falls in children’s reading, which is now at its lowest level on record
  • The National Literacy Trust reports “shocking and dispiriting” falls in children’s reading, which is now at its lowest level on record
  • Our universities are at the front line of this crisis. They are now teaching their first truly “post-literate” cohorts of students
  • “Most of our students”, according to another despairing assessment, “are functionally illiterate”. This chimes with everything I’ve heard in my own conversations with teachers and academics. One Oxbridge lecturer I spoke to described a “collapse in literacy” among his students.
  • The transmission of knowledge — the most ancient function of the university — is breaking down in front of our eyes. Writers like Shakespeare, Milton and Jane Austen whose works have been handed on for centuries can no longer reach the next generation of readers. They are losing the ability to understand them.
  • Laid out on the page their arguments would seem absurd. On the screen, they arepersuasive to many people.
  • Postman cites the Lincoln-Douglas debates of 1858 in which both presidential candidates spoke at incredible length and in remarkable detail as one of the summits of print culture: Their arrangement provided that Douglas would speak first, for one hour; Lincoln would take an hour and a half to reply; Douglas, a half hour to rebut Lincoln’s reply. This debate was considerably shorter than those to which the two men were accustomed . . . on October 16, 1854, in Peoria, Illinois, Douglas delivered a three-hour address to which Lincoln, by agreement, was to respond…When Postman was writing in the late 1980s, such debates were already impossible to imagine.

Marriott’s post is dramatic. Its strength is more in diagnosis than in bridging the decline of traditional literacy to its ramifications.

A librarian writes a terrific criticism of the post which articulates the concern I feel but didn’t put my finger on.

The real crisis isn’t that people can’t focus. It’s that we’ve built information environments actively hostile to contemplation while simultaneously lamenting the loss of contemplative practices. We’ve created attention casinos and then diagnosed the players with moral weakness. This is a design problem masquerading as a cultural catastrophe.

Consider what actually happens in a modern library. We don’t just house books anymore. We create what I think of as “containers for attention”: spaces and practices that enable different kinds of engagement with ideas. The silent reading room remains sacred, but it’s joined by maker spaces where people think with their hands, recording studios where oral traditions find new life, collaborative zones where knowledge emerges through conversation. We’re not abandoning literacy. We’re expanding what literacy means.

Marriott is right that we’re living through a profound transformation. Where he sees collapse, though, I see metamorphosis. The challenge isn’t to preserve the aristocracy of print but to democratise the conditions for deep thought across all modes of engagement. This means designing information environments that support sustained attention, teaching people to navigate multiple modes of meaning fluently, and recognising that human understanding has always been richer than any single medium could contain.

The future Marriott fears, where we’re all reduced to emotional, reactive creatures of the feed, is certainly one possibility. But it’s not inevitable. The teenagers I see who code while listening to philosophy podcasts, who annotate videos with critical commentary, who create elaborate multimedia presentations synthesising dozens of sources: they’re not the degraded shadows of their literate ancestors. They’re developing new forms of intellectual engagement that we’re only beginning to understand.

The question isn’t whether civilisation will survive the death of traditional literacy. It’s whether we’ll have the wisdom and imagination to build institutions, practices, and spaces that support human flourishing in an age where meaning moves through light and sound as readily as through ink. That’s the real work ahead, and it’s far more interesting than mourning a monopoly that was always going to end.

There’s a compromise between Marriott and the librarian. A minority of people will have the “wisdom and imagination” to be empowered by new mediums and not be “reduced to creatures of the feed”.

Maybe it’s not your fault or “moral failing” if you can’t focus when We have decided to outsource our principles to “what’s good for the market is Good”.*


* I’m not sure when this happened but here’s how I see it:

When I was a teen, the Jeff Lebowski played by David Huddleston’s character was the villain. Jeff Bridges’ Lebowski was the hero.

Your revolution is over, Mr. Lebowski. Condolences. The bums lost.

The dude extracts a mini-revenge when he tricks Brandt into giving him an expensive rug.

The spirit of today would be to lock the Dude up for pulling one over on a guy who turned out later to be an empty suit:

We did let him run one of the companies briefly, but he didn’t do very well at it…I give him a reasonable allowance. He has no money of his own. I know how he likes to present himself. Father’s weakness is vanity.

You don’t need to mainline kumbaya to notice how much rebellion-coded acceleration optimism is corporate-cuck fluffery.

Here’s a fun one:

There are only 2 possible reactions.

  1. You hate this interview
  2. You love this interview and hate yourself

I’m still stuck in the 90s, so you can guess where I live on this.


In honor of Jane Goodall, I’ll share a letter I saved in my notes years ago sharing her exhortation to make kids read:

Dear Children,

I want to share something with you — and that is how much I loved books when I was your age. Of course, back then there was no Internet, no television — we learned everything from printed books. We didn’t have much money when I was a child and I couldn’t afford new books, so most of what I read came from our library. But I also used to spend hours in a very small second hand book shop. The owner was an old man who never had time to arrange his books properly. They were piled everywhere and I would sit there, surrounded by all that information about everything imaginable. I would save up any money I got for my birthday or doing odd jobs so that I could buy one of those books. Of course, you can look up everything on the Internet now. But there is something very special about a book — the feel of it in your hands and the way it looks on the table by your bed, or nestled in with others in the bookcase.I loved to read in bed, and after I had to put the lights out I would read under the bedclothes with a torch, always hoping my mother would not come in and find out! I used to read curled up in front of the fire on a cold winter evening. And in the summer I would take my special books up my favorite tree in the garden. My Beech Tree. Up there I read stories of faraway places and I imagined I was there. I especially loved reading about Doctor Doolittle and how he learned to talk to animals. And I read about Tarzan of the Apes. And the more I read, the more I wanted to read.I was ten years old when I decided I would go to Africa when I grew up to live with animals and write books about them. And that is what I did, eventually. I lived with chimpanzees in Africa and I am still writing books about them and other animals. In fact, I love writing books as much as reading them — I hope you will enjoy reading some of the ones that I have written for you.


Money Angle

Below is an excerpt from the presentation I did at McCombs Business School at UT Austin.

It’s more hands-on to watch it after you take this quiz:

Confidence Test

(Respondents tend to score about 4 out of 10 on it.)

There’s a fun experiment in the video as well.

You’ll see just overconfidence and confirmation bias feed off each other in an escalating, reinforcing loop — and the key to stopping it.

Money Angle For Masochists

I was reviewing the posts I’ve written that have gotten the most views over the years. These 5 posts have had the longest tail, presumably because they are evergreen. They get readers every year.

  1. Straddles, Volatility, and Win Rates
  2. Lessons From The .50 Delta Option
  3. Moontower on Gamma
  4. If You Make Money Every Day, You’re Not Maximizing
  5. Understanding Edge

This is the most widely read and shared post I’ve ever written:

Why Investing Feels Like Astrology

As an fyi, all my finance articles are cross-posted on the moontower.ai blog so these URLs are the cross-posted ones. The originals are on the blog. Since a lot of my writing is educational, it doesn’t make sense to be in chronological blog format so while the blog is useful as a host, it’s better organized in this index.

Stay groovy

☮️

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Moontower #287

Friends,

If you read nothing else in today’s letter, hear me now: THANK YOU.

Thank you from me. Thank you from my good friend Jamie’s entire family. Words cannot rise to the occasion.

You will recall a March issue titled Moontower Unite:

I got a distressing text on Tuesday. A close friend I grew up with informed me that her younger brother’s daughter, Rachel, was just diagnosed with AML, a rare aggressive leukemia. Rachel turned 10 this week.

I just sat there. What is there to say? How can I help?

Her little bro Jeff was like my own little bro and now he’s living a nightmare. Not to mention having an 11-year-old daughter who is being passed around the relatives in NJ as the parents will be posted up at Children’s Hospital in Philadelphia for the next 5 months for what is just the preliminary stage of treatment. Daily in-patient chemo.

I went to Twitter and found that the follower community there is amazingly generous and I promised to put this in the letter as well. There’s no pressure.

Jamie texts me again a few days ago with a link to her Facebook:

After admitting she’s been sobbing for 2 straight days, Jamie followed up to send a thank you to all you readers and followers.

I didn’t share the prognosis at the time. Nobody would want to write those words.

So if you responded to either the gofundme or even my later plea for bone marrow donors treat yourself today. To borrow one of my wife’s favorite quotes — you may not be able to change the world, but you can change a world.

And you did.


Exchange Students

For the second time in three years, we participated in a program to host Japanese exchange students for a week.

We do it through local org that brings students a few times a year. Our guests were 2 16-year-old boys, Yuki and Haruto.

Here’s how it works:

  • After some vetting, the org matches you with 2 students and gives you $700.
  • We pick up the boys on Sunday evening. In this program, there was a total of 40 students.
  • We bring them to BART each morning so they can join the rest of the students on a day-long excursion. Some examples included seeing a museum and GG bridge, and visiting Stanford & Cal. We pick them up from BART around 5pm.
  • They leave the following Saturday morning.

Effectively, you hang out with them for 6 evenings. It’s not a big commitment, still we make it a hectic week. We take them out to dinner (burger night, bbq night, taco night, take-out night where we get pizzas from multiple places for a taste test), go bowling, host gatherings with Japanese-speaking friends (we did that on 2 separate nights). We take them shopping as they always want to buy gear. The Dick’s Sporting Goods excursion has never failed.

Navigating the language barrier is part of the adventure. The upside of this is the bonding. It is remarkable how memorable both Yinh and I and our boys find this. They still refer to Mihiro and Tomonuri who we hosted in 2023. In fact, the boys stay in touch Yinh via IG and even reached out when we posted the photos of our latest guests.

There’s a ritual where the students give gifts from Japan and share the notes their parents send. This is one of my favorite things…to read what someone says about their babies that they send over. Neither of our guests had ever left Japan until this trip. Imagine writing that note.

We send them home with lots of swag and notes back to their parents telling them how well-mannered their sons are (which is impossible to exaggerate). It’s delightful to hear about their families, upbringing, what they want to study or do when they grow up. And of course, to see the questions and thoughts it prompts in our own kids. After the 2023 visit our boys wanted to learn a foreign language because when they saw their Japanese friends talking to our visitors, it looked like a superpower. Since then, they have been enthusiastic students of Vietnamese and now have a secret language with mom and grandma that daddy doesn’t understand.

I could go on, but it’s one of those things that you either think sounds cool or doesn’t, I just want to remind you that it exists. I think it’s great for families with kids, but I also noticed that there’s a lot of empty-nesters at the pickup. Not a bad way to bring the sound of voices back into a house that’s too big for a couple.

Oh and a fun thing I just learned yesterday as we were chatting about our guests with good friends who live in Texas, who also had a memorable bond with their Japanese students: this summer when visiting Japan for their son’s baseball tourney, their students’ whole family flew to see them and watch the games!


Money Angle

My wife has a pet project that involves very candid conversations about money matters with other women.

Think of today as a PSA born from a bit of advice she gives surprisingly too often:

Do not have meaningful amounts cash sitting idly in a bank account.

Outside of the cash you leave in your checking account for covering regular ebbs and flows in receipts and expenses, keep any extra cash you don’t want to invest in T-bills. Especially, if you live in NY, CA, NJ, etc.

T-bills are state-tax exempt, but high-yield savings account are not.

You can buy T-bills through most brokerages (I’ve taught so many people in my extended family how to do this) .

Alternatively, you can buy short-term T-bill ETFs like BIL, VBIL, or SGOV. You can buy ETFs just like you buy stocks — through your brokerage as well. The interest is paid via monthly dividends and it’s still state-tax exempt.

A woman told my wife this week — “I think talking to you just made me like $10,000.”

The wife’s project reminds me how many false assumptions I have about what is common knowledge around money.

Money Angle For Masochists

Ilia Bouchev ran oil trading for Koch for over 20 years. I’ve traded oil and related derivatives more than anything else in my career. This interview with Rory Johnston is terrific. Ilia is giving the straight scoop, so you should just listen if you are at all curious about oil trading.

Just one brief comment from me:

Ilia talks of fundamentals still mattering, but you are mostly trading the “reaction function”. I think this is a great way to understand equities trading. It feels like it’s all flows and reaction function because the realized fundamentals are so far in the future, beyond the horizon of useful feedback loops if you are trying to trade on fundamentals.

[One can invest on fundamentals, meaning underwriting some far future of the world, but not with the signal-to-noise you can verify from high turnover trading strategies.]

From My Actual Life

While our exchange students bid us farewell yesterday, this week, much of my east coast fam is visiting to celebrate a cousin’s wedding in Napa. It’s a nice season to get married. In fact, Yinh and I celebrated 16 years on October 2nd 🙂

I mentioned my wife’s pet project about money matters. As you can imagine, how couples deal with money, joint accounts, budgets is one of the main themes.

I’ll share a little about our approach to finance in no particular order.

Do we have a prenup?

Nope.

We both started with nothing but college debt. Neither of us is in line for a meaningful inheritance and in fact both provide financial support to at least some of our parents. We met on the day I turned 25 and she is a few years younger. We didn’t have an imbalance in career prospects like me being a trader and her being a teacher. We both had real upside. I say that as a backdrop for why we wouldn’t even have considered a prenup. We felt like we were in similar situations. But this left-brain explanation is secondary to just — being against the idea. Classic YMMV situation.

Do we have separate accounts?

No. There is literally no concept of mine vs hers. That even goes for spending. I ordered a $300 guitar pedal yesterday and told her because I feel compelled to tell her anytime I spend say more than $100 on something that is only for me. Her reaction every time I do that is, “If I told you every time I spent a few hundred bucks on something for myself, you’d be upset”.

Which brings me to…

Do we have a budget?

Wellllll…it’s more like guidelines.

7 or 8 years ago I did an exercise…I reviewed all our spending for a year. Yinh called it The Audit. I wanted to understand what it cost to wake up in the morning the way we were living. We looked at where we were spending to decide if it was in line with our priorities both in the consumption sense (was X dollars on travel acceptable) and in terms of our savings rate (or what I think of as giving our future selves a say in our current spending).

The value of the exercise was mostly understanding where our money was going so that in the future we can know if and how much creep we were allowing. The knowledge was useful because it was a chance to “sign off” on how things were going. We deemed the pressure it put on us acceptable with regard to our wider financial picture, prospects, and ambitions.

The exercise also had an unanticipated benefit. It stopped me from caring about any single transaction. If you don’t do the exercise it’s hard to put the splurge in context of how much it moves your annual nut. If Yinh’s self-care expenditures dwarf the cash that I spend on myself, but we’re already ok with the composition of our overall spending then why should I care? We’re on track.

It’s changed my entire neurosis about money. I quote Walter all the time: “I’m shomer shabbos…I don’t handle money”. As long as I feel like my spending habits are in line to what they’ve been, I don’t think about day-to-day money. Yinh is the one who looks at bank balances and credit cards regularly (part of this is admittedly good hygiene — catching errors etc, but part of it is to satisfy her money neuroses).

I only review everything during tax prep season. This gives me the chance to see if my “feeling that my spending habits” are constant is well-calibrated. Instead of giving money daily mindshare I give it a dedicated time for review.

Who manages our investment portfolio?

I handle the general portfolio allocation. I track the running portfolio vol and correlations for public/liquid investments. About 2 weeks after each quarter end, I update the marks on any private funds, and record all bank balances. It serves as a quarterly net worth check-in.

[For angel investments, I don’t update marks unless there’s a downward revision. Marks are at cost. Never up.]

“Taking the pulse” every quarter is more of a Yinh-requirement than mine. I’d be fine with every 6-months and very likely just every tax season. However, I think you can spot red flags in private funds if you look quarterly, so it’s easy to agree with her without feeling like I’m just patronizing her neurosis.

Investment ideas can come from either of us. I just manage the asset allocation around whatever we add/subtract.

For investments that represent less 1% of assets we don’t really need to discuss them, but we usually do anyway. We’re both curious about investing generally which is probably not going to be the case if 1 or zero partners is in finance.

Who is more spendy?

For ordinary matters, Yinh by far. With my family coming this week she wanted to rent a mechanical bull and tequila donkey or something for a backyard party. I’m the circuit breaker. I put the kabash on that. Instead, she bought Tornado foosball table off FB marketplace. Facepalm.

She’s definitely the minister of fun on regular life. The Japanese exchange program was even her idea.

My wiring is too ascetic. On an intellectual level, I think that wiring is faulty, so I appreciate that she’s this way. I push back, we land somewhere in the middle, both finding an acceptable mix of responsibility and joy.

When it comes to big-ticket items, I’m the spendier one. I was way more comfortable with budget for our new house. I pushed for a larger budget for the wedding. We are already going over budget on the ADU design and Yinh is the one imposing discipline.

I don’t have any convincing hypothesis for the difference in our biases.

(For mine, I’d guess there’s some sense that spending big on non-recurring items feels like less of a lifestyle-creep risk than frequent, smaller splurges. I’m not even convinced by that logic though.)

Microcosm of marriage

Differences abound. If your relationship is worth it, you make them manageable. Disagreeing on that fact is the only difference that cannot be managed.

Seeing your partnership from the facet of money is a reminder that you didn’t marry yourself. And that, my friends, is worth celebrating.

 

16 years from this day…

I get this…

That’s me and my 9-year-old playing on a stage together for the first time.

 

There’s no mystery about what I’m supposed to do in life. Resolve to deserve what I have. I’ll never get there, but that’s the type of goal that keeps me alive.

 

Stay groovy

☮️

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