Moontower #166

One of my deepest held beliefs is that our need for coherence is a profound source of misery. We agitate for universal theories to tie everything together. Our obsessions with gurus, religion, ideology, macro, or even astrology are symptoms. We search for meaning as if it is something that’s “out there” to be discovered. I’m not holding my breath.

These quests are actively destructive when taken too seriously. When people become overly invested in any of these expeditions, we are sentenced to watching the mental gymnastics routines their precious egos cling to. It’s worse than just being cringe. It’s insidious. They dehumanize opposition so they don’t even have to consider reasonable antagonistic stances.

I just picked up Simone de Beauvoir’s book The Ethics Of Ambiguity because its description vibrates with my own feelings. I’ll report back after reading it.  (See How The Need For Coherence Drives Us Mad to see if you’d be interested in reading it.)

In the meantime, I’ll share a technique that I use to resist the seduction of coherence.

A Drawer Of Curiosities

In my notes, I keep an ever-growing list of “tensions” and “paradoxes” that I encounter from reading or experience. It is a constant reminder that every bit of advice you’ve ever heard is not universal. My buddy Jake likes to say that seat belts are the only free lunch. To which I respond, “unless the presumption of safety encourages drivers to speed or drive more recklessly”. Let’s be blunt. My response is utter ankle-biting tediousness (what I call tedious some people consider their personality). The larger takeaway is there are paradoxes running loose everywhere and if we run around trying to corral them with some ill-conceived notion that it makes us “more right” or there are truths we can somehow own and wield, then we’ve done nothing but build intellectual totems to hubris.

Instead of trying to resolve the paradoxes, maybe just accept them. Name it to tame it, put it in a drawer, and move on. You don’t need the world to bend around your own brain to protect your ego. You can just have a big list that reminds you that the task is futile. That’s the antidote.

[See A Drawer Of Curiosities for excerpts from a couple of studies that speak to the benefits of acknowledging and living with paradox. I have long thought this was important and was discussing it with a friend who said there’s actually some biology behind our resistance of paradox. They sent me the links found in the appendix of that post.]

Graveyards

I keep another type of list that is unexpectedly satisfying. A graveyard of ideas and projects that I’ve abandoned. It’s a form of closure. It’s a form of loving and losing. There’s no need for shame or regret because you didn’t learn to play the guitar or start that business. Most text editors have a “strikethrough”. Use it.

The things you actually did instead were a filter. They revealed your priority. (If you have a problem with your priorities that’s a separate issue). By acknowledging that you will only execute on a fraction of your ideas, you lower the stakes of having ideas, and the more ideas you allow yourself to have, the more fun life will be.

A close-minded young person feels tragic. But weirdly, I think it’s even more tragic for older people whose years give them a perch to see how wide a range of experience exists across the world and its people — and then they ignore that information. It’s like locking yourself in a room with 1 friend, setting the thermostat to your preferred temperature, throwing away the key, and talking about the same old shit until you die.

Take chances intellectually and in life. List them. If there’s nothing on the list, maybe fix that. You still have time before you yourself are in a graveyard.

Scavenger Hunt

In How to turn problems into a curiosity engineAnn-Laure Le Cunff describes a fun game renowned physicist Richard Feynman played as he navigated life:

One of Feynman’s most enduring characteristics was that he loved problems. Instead of avoiding them or trying to solve them as fast as possible, he would seek interesting problems, keep them in mind, let them simmer, and constantly try to connect his everyday experiences to these big questions.

“You have to keep a dozen of your favorite problems constantly present in your mind, although by and large they will lay in a dormant state. Every time you hear or read a new trick or a new result, test it against each of your twelve problems to see whether it helps.”

Similar to Alice who discovers a strange world through the looking glass, the questions you choose to keep in mind act as a mirror that reflects the world around you and makes you look beyond the surface of the glass.

Your favorite problems form a prism that separates incoming information into a spectrum of ideas — a frame that allows you to deliberately filter distractions, direct your attention, and nurture your curiosity. In short, your favorite problems become a curiosity engine.

Creating a list of favorite problems offers many benefits:

  • Turn stressful situations into intriguing problems to explore
  • Filter information based on whether it relates to one of your favorite problems
  • Connect with fellow curious minds who are interested in similar problems
  • Focus your attention on ideas that arouse your curiosity
  • Notice relevant patterns and potential solutions across seemingly unrelated topics

Let’s ignore yet another advice tension (Feynman is unknowingly inviting people to double-down on confirmation bias) to give this idea respect. Feynman is saying “life is a scavenger hunt.” It wouldn’t be fun if you knew where everything belonged. If everything just snapped into place.

Instead of starting with airtight beliefs, go trick-or-treating. The questions are your plastic pumpkin and the world’s wonders are the candy. Surprises will taste sweet if you are looking to grow, and bitter if you are afraid.

Like Halloween, you choose who you want to be.


Money Angle

Personal portfolio update: We closed on the sale of the Texas property we bought in Summer of 2021 this past week. The sale took a long time because showing it was a bit of a challenge with tenants. We asked an aspirational price in the Spring, probably 6 weeks too late to catch the insanity but still got a bid through the asking price. Unfortunately, the stock market dropped and 4 days later the buyer pulled out. We cut the home price 10%, and got into another contract quickly, but then the closing took 2 months. Alas, it’s done. We put about 40% of the proceeds into homebuilders and a world ETF and the balance in 4% t-bills. We will have a chat with our accountant this week about end-of-year tax management (selling investments that have gotten crushed in taxable accounts to offset gains on the property. Should be educational.)

Moving on…

Investing is hard. It’s a game in a complex environment. It’s hard to tell a bad decision from a good decision just based on the outcome because it’s a low signal vocation.

That said, I’ve harbored some suspicion that analytically-weak investment managers would find it convenient to hide behind those concessions. Synthesizing decisions in an open environment is much harder than solving a problem set. But what if you can’t even solve a problem set? Am I supposed to believe you can do all the hard stuff, but just choked on the solvable stuff?

This isn’t the first time I’ve wondered this. See Can Your Manager Solve Betting Games With Known Solutions?

Today’s post is in a similar vein.

Bet Sizing Is Not Intuitive (8 min read)

Humans are not good bettors.

It takes effort both in study and practice to become more proficient. But like anything hard, most people won’t persevere. Devoting some cycles to improve will arm you with a rare arrow in your quiver as you go through life.

Skilled betting demands 2 pivotal actions:

  1. Identifying attractive propositions

    This can be coded as “positive expected value” or “good risk/reward”. There is no strategy that turns a bad proposition into an attractive one on its own merit (as opposed to something like buying insurance which is a bad deal in isolation but can make sense holistically). For example, there is no roulette betting strategy that magically turns its negative EV trials into a positive EV session.

  2. Effective bet sizing

    Once you are faced with an attractive proposition, how much do you bet? While this is also a big topic we can make a simple assertion — bad bet sizing is enough to ruin a great proposition. This is a deeper point than it appears. By sizing a bet poorly, you can fumble away a certain win. You cannot afford to get bet sizing dramatically wrong.

Of these 2 points, the second one is less appreciated. Bet sizing is not very intuitive.

To show that, we will examine a surprising study.

The Haghani-Dewey Biased Coin Study

In October 2016, Richard Dewey and Victor Haghani (of LTCM infamy) published a study titled:

Observed Betting Patterns on a Biased Coin (Editorial from the Journal of Portfolio Management)

The study is a dazzling illustration of how poor our intuition is for proper bet sizing. The link goes into depth about the study. I will provide a condensed version by weaving my own thoughts with excerpts from the editorial.

The setup

  • 61 individuals start with $25 each. They can play a computer game where they can bet any proportion of their bankroll on a coin. They can choose heads or tails. They are told the coin has a 60% chance of landing heads. The bet pays even money (i.e. if you bet $1, you either win or lose $1). They get 30 minutes to play.
  • The sample was largely composed of college-age students in economics and finance and young professionals at financial firms. We had 14 analyst and associate-level employees of two leading asset management firms.

Your opportunity to play

Before continuing with a description of what an optimal strategy might look like, we ask you to take a few moments to consider what you would do if given the opportunity to play this game. Once you read on, you’ll be afflicted with the curse of knowledge, making it difficult for you to appreciate the perspective of our subjects encountering this game for the first time.

If you want to be more hands-on, play the game here.

Devising A Strategy

  1. The first thing to notice is betting on heads is positive expected value (EV). If X is your wager:

    EV = 60% (x) – 40% (x) = 20% (x)

    You expect to earn 20% per coin flip.

  2. The next observation is the betting strategy that maximizes your total expected value is to bet 100% of your bankroll on every flip.
  3. But then you should notice that this also maximizes your chance of going broke. On any single flip, you have a 40% of losing your stake and being unable to continue this favorable game.
  4. What if you bet 50% of your bankroll on every flip?

    On average you will lose 97% of your wealth (as opposed to nearly 100% chance if you had bet your full bankroll). 97% sounds like a lot! How does that work?

    If you bet 50% of your bankroll on 100 flips you expect 60 heads and 40 tails.

    If you make 50% on 60 flips, and lose 50% on 40 flips your expected p/l:

1.560 x .5040 = .033

You will be left with 3% of your starting cash! This is because heads followed by tails, or vice versa, results in a 25% loss of your bankroll (1.5 * 0.5 = 0.75).

This is a significant insight on its own. Cutting your bet size dramatically from 100% per toss to 50% per toss left you in a similar position — losing all or nearly all your money.

Optimal Strategy

There’s no need for build-up. There’s a decent chance any reader of this blog has heard of the Kelly Criterion which uses the probabilities and payoffs of various outcomes to compute an “optimal” bet size. In this case, the computation is straightforward — the optimal bet size as a fraction of the bankroll is 20%, matching the edge you get on the bet.

Since the payoff is even money the Kelly formula reduces to 2p -1 where p = probability of winning.

2 x 60% – 1 = 20%

The clever formula developed by Bell Labs researcher John Kelly:

provides an optimal betting strategy for maximizing the rate of growth of wealth in games with favorable odds, a tool that would appear a good fit for this problem. Dr. Kelly’s paper built upon work first done by Daniel Bernoulli, who resolved the St. Petersburg Paradox— a lottery with an infinite expected payout—by introducing a utility function that the lottery player seeks to maximize. Bernoulli’s work catalyzed the development of utility theory and laid the groundwork for many aspects of modern finance and behavioral economics. 

The emphasis refers to the assumption that a gambler has a log utility of wealth function. In English, this means the more money you have the less a marginal dollar is worth to you. Mathematically it also means that the magnitude of pain from losing $1 is greater than the magnitude of joy from gaining $1. This matches empirical findings for most people. They are “loss-averse”.

How did the subjects fare in this game?

The paper is blunt:

Our subjects did not do very well. Suboptimal betting came in all shapes and sizes: overbetting, underbetting, erratic betting, and betting on tails were just some of the ways a majority of players squandered their chance to take home $250 for 30 minutes play.

Let’s take a look, shall we?

Bad results and strange behavior

Only 21% of participants reached the maximum payout of $250, well below the 95% that should have reached it given a simple constant percentage betting strategy of anywhere from 10% to 20%

  • 1/3 of the participants finished will less money than the $25 they started with. (28% went bust entirely!)
  • 67% of the participants bet on tails at some point. The authors forgive this somewhat conceding that players might be curious if the tails really are worse, but 48% bet on tails more than 5 times! Many of these bets on tails occurred after streaks of heads suggesting a vulnerability to gambler’s fallacy.
  • Betting patterns and debriefings also found prominent use of martingale strategies (doubling down after a loss).
  • 30% of participants bet their entire bankroll on one flip, raising their risk of ruin from nearly 0% to 40% in a lucrative game!

Just how lucrative is this game?

Having a trading background, I have an intuitive understanding that this is a very profitable game. If you sling option contracts that can have a $2 range over the course of their life and collect a measly penny of edge, you have razor-thin margins. The business requires trading hundreds of thousands of contracts a week to let the law of averages assure you of profits.

A game with a 20% edge is an astounding proposition.

Not only did most of our subjects play poorly, they also failed to appreciate the value of the opportunity to play the game. If we had offered the game with no cap [and] assume that a player with agile fingers can put down a bet every 6 seconds, 300 bets would be allowed in the 30 minutes of play. The expected gain of each flip, betting the Kelly fraction, is 4% [Kris clarification: 20% of bankroll times 20% edge].

The expected value of 300 flips is $25 * (1 + 0.04)300 = $3,220,637!

In fact, they ran simulations for constant bet fractions of 10%, 15%, and 20% (half Kelly, 3/4 Kelly, full Kelly) and found a 95% probability that the subjects would reach the $250 cap!

Instead, just over 20% of the subjects reached the max payout.

Editorialized Observations

  • Considering how lucrative this game was, the performance of the participants is damning. That nearly one-third risked the entire bankroll is anathema to traders who understand that the #1 rule of trading (assuming you have a positive expectancy business) is survival.
  • Only 5 out of the 61 finance-educated participants were familiar with Kelly betting. And 2 out of the 5 didn’t consider using it. A game like this is the context it’s tailor-made for!
  • The authors note that the syllabi of MIT, Columbia, Chicago, Stanford, and Chicago MBA programs do not make any reference to betting or Kelly topics in their intro finance, trading, or asset-pricing courses.
  • Post-experiment interviews revealed that betting “a constant proportion of wealth” seemed to be a surprisingly unintuitive strategy to participants.

Given that many of our subjects received formal training in finance, we were surprised that the Kelly criterion was virtually unknown among our subjects, nor were they able to bring other tools (e.g., utility theory) to the problem that would also have led them to a heuristic of constant-proportion betting. 

These results raise important questions. If a high fraction of quantitatively sophisticated, financially trained individuals have so much difficulty in playing a simple game with a biased coin, what should we expect when it comes to the more complex and long-term task of investing one’s savings? Given the propensity of our subjects to bet on tails (with 48% betting on tails on more than five flips), is it any surprise that people will pay for patently useless advice? What do the results suggest about the prospects for reducing wealth inequality or ensuring the stability of our financial system? Our research suggests that there is a significant gap in the education of young finance and economics students when it comes to the practical application of the
concepts of utility and risk-taking.

Our research will be worth many multiples of the $5,574 winnings we paid out to our 61 subjects if it helps encourage educators to fill this void, either through direct instruction or through trial-and-error exercises like our game. As Ed Thorp remarked to us upon reviewing this experiment, “It ought to become part of the basic education of anyone interested in finance or gambling.”


I will add my own concern. It’s not just individual investors we should worry about. Their agents in the form of financial advisors or fund managers, even if they can identify attractive propositions, may undo their efforts by poorly sizing opportunities by either:

  1.  falling far short of maximizing

    Since great opportunities are rare, failing to optimize can be more harmful than our intuition suggests…making $50k in a game you should make $3mm is one of the worst financial errors one could make.

  2. overbetting an edge

    There isn’t a price I’d play $100mm Russian Roulette for

Getting these things correct requires proper training. In Can Your Manager Solve Betting Games With Known Solutions?, I wonder if the average professional manager can solve problems with straightforward solutions. Never mind the complexity of assessing risk/reward and proper sizing in investing, a domain that epitomizes chaotic, adversarial dynamics.

Nassim Taleb was at least partly referring to the importance of investment sizing when he remarked, “If you gave an investor the next day’s news 24 hours in advance, he would go bust in less than a year.”

Furthermore, effective sizing is not just about analytics but discipline. It takes a team culture of truth-seeking and emotional checks to override the biases that we know about. Just knowing about them isn’t enough. The discouraged authors found:

…that without a Kelly-like framework to rely upon, our subjects exhibited a menu of widely documented behavioral biases such as illusion of control, anchoring, overbetting, sunk-cost bias, and gambler’s fallacy.

Conclusion

Take bet sizing seriously. A bad sizing strategy squanders opportunity. With a little effort, you can get better at maximizing the opportunities you find, rather than needing to keep finding new ones that you risk fumbling.

You need to identify good props and size them well. Both abilities are imperative. It seems most people don’t realize just how critical sizing is.

Now you do.


Last Call

Trevor Noah is leaving the Daily Show. December 8th is his last episode. Noah is one of my favorite observers of humanity.

I know who I want to take the baton.

Comedian Mo Amer.

I’ve been watching his show Mo on Netflix but just watched his 2018 stand-up special Vagabonding. It reminded me of Noah’s Afraid Of The Dark special.

I have a weak spot for comedians that can do voices (and for that matter, I also love it when animals are anthropomorphized with voices. Think any talking animal in a Super Bowl ad. It’s catnip to me.)

Moontower #165

I just got back from the StockSlam Sessions in NYC. It was an epic week of meeting new friends, seeing old faces, and doing something I haven’t done since my 20s — going home at 2 am four nights in a row. If I were drinking these days I could never have done that at this age (not to mention fitting a workout in on 2 mornings).

The sessions themselves were a raging success. The feedback on both fun and learning was super encouraging, so we have plenty to chew on. I’ll circle back on that when it makes sense.

I wasn’t in the writing jumpseat all week so today is a brief one.

An empathetic thought


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Money Angle

Last Sunday, I mentioned for October I’ll be stringing together a few non-technical posts about trading. Last week I published Trading Vs Investing.

This week I give you:

Celibacy Vs Condoms: The Answer To Whether You Should Trade Options (17 min read)

Here’s the table of contents:

1 Think Before You Even Get Aroused

2 Why Anyone Would Trade An Option?

3 Wear a Condom

4 Conclusion


Last Call

Some random stuff I enjoyed:

  • Notes From An Interview With Serial Entrepreneur Keith Schacht (7 min read)

    I liked the attitude and insights in this pod and took some notes.

  • The Midwit Trap: Why are we so dismissive of simple solutions? (philo.substack)

    This is a cool post demonstrating how people outsmart themselves. A few vectors in particular:

    • Confusing complex for smart
    • Misdiagnosing Pareto distributions
    • Ignoring bottlenecks (ie Theory of Constraints)
    • How “we share 99% of our DNA with chimps” reminds us that just 1% can be a giant difference
    • Hidden “divide by zero” problems where long logic chains become fragile because they rely on every statement being true (this one reminds me of why quarantining risk is an underappreciated tactic — see I Felt Bad For Picking My 3rd Grader Off)

From My Actual Life

Shout out to Chris and Avi who got me to my first death metal show. It was at Monarch in Brooklyn and was headlined by Blood Incantation. Loved the “leave it all on the field” performance. They performed 4 long songs with super-heavy, psychedelic grooves. The drummers of these bands are aliens.

The names of the other bands are also morbid MadLibs:

Full Of Hell, Vermin Womb, Mortuous and God Is War

Stay friggin groovy!

Moontower #164

I threw a $500,000 purchase price and a 7% 30-year fixed rate into a mortgage calculator. That’s a payment of $3,327.

Earlier this year, if you secured a mortgage at 3%, you could have bought a home for $790,000 and had the same payment.

Since housing hasn’t dropped 36% this year homes have gotten much more expensive to own. Considering you can buy 1-year t-bills yielding 4% that are state-tax free and nominally risk-free, the investment case for RE is looking pretty poor unless rents skyrocket or real estate craters to bring cap ratios back up.

If the higher rate environment leads to a recession and lay-offs then I’m doubtful that rent increases are going to be the primary normalization pathway. It feels like employment trends will be a clue to how quickly housing will re-price lower (it’s already started of course). The yield curve is inverted, so the bond market is suggesting that the rate hikes in the near term will slow inflation and the economy.

This is all just simple observation. Like looking out the window. And as one does, when they sit at a window, one muses. And muse I shall.

Musing #1: Bid-Ask Widening

A year ago the people that paid ridiculous prices for RE were market orders. “Fill me at any price”. Many of them were immediately in the money (ie they probably could have turned around and sold a month later for more. Maybe not net of transaction costs but you get the idea). This isn’t shocking. When optimism turns to euphoria, the rate of change of the returns themselves can explode into a parabolic curve. Of course, such curves are unsustainable. The smug moment of being in the money is short-lived in the same way that a fund that buys a ton of stock going into the close usually gets a favorable mark on their daily p/l. Their sloppy buys drove the price higher in a short period of time. The real sellers didn’t have time to react before the close. But as soon as they check the comps overnight, you can be sure the supply is coming tomorrow morning.

I think of it like water going down a drain…once most of the water is through the drain the remaining liquid swirls quickly around the drain before you hear that sucking sound. Whoosh. The last bid is filled. With maximum punnage — the liquidity is gone.

In the meantime, many other buyers were priced out. You can think of them as limit bids. It’s an imperfect analogy but it will suffice. As things go south now, some of those bidders might be anchored to their original bids which were “cheaper” than where the home traded. However, if they get filled on the way down, they actually have more negative edge even though they got this theoretical house for a cheaper price than the original buyer. You could belabor this with a stylized model but understanding this concept is a big step towards understanding trading.

Anyway, the old limit bids are probably the new ask and the real bid/ask spread is wide. Prospective buyers are adjusting their bids much lower to keep the monthly payment constant or at least manageable, but sellers who likely have cheap financing from the prior low rate regime do not have to cross the spread. If current prices are 5% off their highs but the new mortgage math means homes they should be 20% lower (similar to the stock market) the current listing prices are the “asks” of a wide market.

Buyers lifting those offers are giving up edge for convenience/immediacy. That’s the usual reason people willfully give up edge for anything. Sellers hitting bids either need to (relocation, getting laid off, divorce, or any other life thing that shuffles liquidity needs) or they think rents aren’t going to increase as part of the normalization process.

Musing #2: Price Can Ruin Any Investment Idea

Always promotional, the real estate industry in an effort to pump bids, always finds an angle. They look at CPI and rates increasing, and peddle “RE is an inflation hedge”.

I mean, sure. But price matters.

By that logic, RE was also an inflation hedge 6 months ago, so are real estate prices supposed to be higher today given the elevated inflation of the past 6 months?

A few weeks ago Tom Morgan published Eight Investing Gems, which was a list of underappreciated, evergreen concepts sourced from investment professionals. I was flattered to be asked and my response fit well here:

Markets are biology, not physics, and that’s important because every good idea can be ruined by price. For example, real estate with a mortgage might be a good inflation hedge, but if history has taught everyone that lesson then it will be less true going forward. In other words, the price today already incorporates that (imagine paying 3x for your current home… how’s that going to work out as an inflation hedge?)

Prices are what matter. Not blanket, lazy sentences like “RE is an inflation hedge”. You’re not trading sentences.

[It’s also not clear that RE is an inflation hedge during periods of inflation]

Musing #3: Bullwhips Everywhere All The Time

Investopedia:

The bullwhip effect refers to a scenario in which small changes in demand at the retail end of the supply chain become amplified when moving up the supply chain from the retail end to the manufacturing end.

With Covid closings followed by re-opening, this effect has received lots of attention. It’s not new. The famous beer game lets you play as a retailer, distributor, manufacturer, or wholesaler to make ordering decisions that balance your inventory against your customer’s demand. Orders are a proxy for demand, but the lag times in delivery lead to over and underreaction in ordering decisions.

Bullwhips feel like an apt analogy for the over and under reactions that happen in our largest markets:

  1. The underbuilding of homes since the GFC. Builders’ PTSD and higher lending standards for the past decade have contributed to a housing shortage. In the past, I might have associated building velocity with the credit cycle, but the excess of the mid-aughts seemed to have chastened builders despite the loose monetary conditions of the 2010s.
  2. Energy prices, in the wake of shale’s “growth at all costs”, busted in the mid-2010s. They surged back recently as the reality that fossil fuel transition will take longer than expected has collided with underinvestment in production. Drillers were scolded both from their investors (overproduction) and would-be investors (ESG).

[Just FYI, def not advice:

I sold my energy overweights in the Spring and recently started dollar-cost-averaging back in as I add investment exposure in this pullback. Overall, still overweight cash which I’ve been moving directly into T-bills. I’m in the midst of trying to do a rebalance from RE to equities but need one leg to close first so I don’t get middled. I hate illiquidity. In case curious, my prior energy exposure was XLE in an IRA, but I’m re-entering via deferred WTI futures. Instead of a div yield, you get a theoretical roll return. I am not an especially active trader/investor so I figure I’ll share stuff like this when I’m actually doing something. Again, I’m more weighted in cash than most sane people and don’t consider myself a good investor — I mostly try to avoid disaster. I just want to have my assets match my future liabilities — if I want to get rich, I’ll try a higher signal route of relying on myself not random number generators.]

  • Musing #4: Too Many Assholes Playing A “Loser’s Game”

Read this essay:

Too Many Assholes (7 min read)
by Jared Dillian

Jared is an author. He’s published a couple books, one was fiction. He was an index trader for about a decade before becoming a full-time writer amongst many endeavors. Jared is an exceptional financial writer. I read his professional letter regularly for most of the past decade.

This particular essay starts out:

This will be the only financial essay I write, I promise.

His substack is about culture and life not investing. So when he paused to write a single finance post in this collection, I paid attention. It felt very familiar. It has the same feel as his paid daily writing.

I want to offer a perspective on his writing. When people ask him for a free sample of the paid letter he doesn’t give them out. It’s for the same reason I give when people ask me if they should sub to his letter. The individual letters are not useful if you are looking for a great stock tip or definitive proof that the letter will make you money. So if you ask for a single letter, you miss the point. He’s capturing the broad strokes and he’s repetitive. And this is valuable in its gestalt.

I’ll re-hash my Twitter thread on Jared’s post:

This essay could have been called “play the cards not the man” but Jared is a snappier writer so he cut to the heart. It sounds like a folksy kind of essay but it’s deep. If you can internalize his essay you risk making small mistakes, you’ll almost definitely get the timing wrong, but there will be no catastrophes. Since survival is the goal in what Charley Ellis called the “loser’s game” this essay is an irreverent treatise in financial self-preservation.

Jared brings up contrarianism which by definition is required fo outsized returns. But at the turns in markets, the contrarian instinct is defensive. Yes, it can be expensive mid-trend but I’m not advocating for perma-contrarianism anyway. Sometimes contrarianism is common sense when LPs in private funds are climbing over each other to pay 20x revenue for profitless companies.

Options trading provides a well-balanced education in contrarianism. You spend a lot of time fading “point spreads that went too far” so you learn to deal with the discomfort of positions that are against the crowd. And of course, you do need to manage risk around that carefully (position limits are key because once a price enters la-la land there’s no restraint on it go to la-la-la land). At some point, you are selling because you are approaching “there’s nobody left to buy” territory and that is the exact point in time when it’s hardest to do that.

Playing the hindsight game, in the Spring I sold my energy stocks (a touch early but again it was a small mistake) despite being bullish. The thinking: Everything about oil looks bullish but everyone else sees that too. It’s insane to be bearish. But then you have to switch into the mind of a seller…there is no opening seller. So the price must contain a massive premium in it to attract any sell flows.

And that is enough to pull the trigger to sell for me. Yes, I could be wrong, but the risk/reward said “sell”. No fundamentals. Pure psychology.

[This isn’t any kind of victory lap. I’m losing money because I’m basically a long only investor and my current life is not a trading seat where I have the advantage of being in the mix.]

The question to focus on is “What psychology is in the price?” The price includes all the spreadsheets already. It’s the sum of the emotions and the nerds.

Jared focuses on sentiment. It’s not too useful when the game is played near the 50-yard line. In that zone, I’m perfectly fine to outsource to passive collection of market risk premium. With stocks, you know the proposition — earn 5% over the risk-free rate, give or take 15%, and experience a double-digit peak-to-trough drawdown every other year, and something like a 50% drawdown once a decade. Fat tails. That’s the deal. Over the long-run you’ll make money, but sizing that proposition is a personal matter.

The psychology matters more at the turns. The edges of the field. Marching through the redzone, from the 20-yard line to the goaline, can feel dramatic in compounding space. The 5-yard line to the goaline — this is the blow off top in Doge or the Volkswagon short squeeze in 2008…where the bulk of a total return can come from a short time. This is when things are obviously unstable. Sticking around to find out which down is gonna be the pick-6 is baggie roulette.

You don’t need to be some market genius when things feel crazy. Just realize that the only way the price can make sense is if someone crazier came along. Unless you have a very special edge in that game (I suspect at these critical turns the internal mechanics of liquidity are understood by a handful of insiders/clearing firms/exchanges, perhaps it’s a short squeeze, that connect the trading world to the credit/banking world. If that’s the case, you, sitting at home in your pajamas, are playing no-limit hold’em with a worse than random hand against people who know their cards.)

If you don’t have a hero instinct and just try to get the broader picture roughly right you can avoid the giant mistakes. That’s 95% of the battle. 2021 was stupid euphoria. That was obvious even in real-time. Sure you could have been early to that realization and looked foolish for a while but zoom your perspective out and ask yourself:

“Am I feeling fomo or fear?”

That will tell you what everyone else feels and that tells you what’s in the price. You know what that’s called: empathy. You are putting yourself in the minds of others and therefore the price. It sounds like soyboi shit. But that shit is full is wisdom if you can channel it.


Today’s letter is brought to you by the team at Mutiny Fund:

How can you access a multi-asset strategy concerned with protecting assets and growing long-term wealth?

The Cockroach Strategy seeks to achieve higher long-term, compound growth compared to traditional stock/bond-focused portfolios with more limited drawdowns. ​ It is intended as a total portfolio, a ‘set it and forget it’ approach that strives to give investors peace of mind and meaningful capital appreciation.

The Cockroach strategy consists of a diversified ensemble of assets including stocks, bonds, commodity trend strategies, long volatility strategies, and gold. It is designed to perform across multiple macroeconomic environments: growth, recession, inflation and deflation.

The Cockroach strategy gives investors exposure to asset classes designed to perform in each of those environments including stocks, bonds, commodity trend strategies, long volatility strategies, and gold.

Click Here to Learn More

Disclaimer: Investing is risky, and you are reminded that futures, commodity trading, forex, volatility, options, derivatives, and other alternative investments are complex and carry a risk of substantial losses; and that there is no guarantee the strategy will perform as intended.


Money Angle

I’ll be squirting out some new posts about trading over the next weeks. They aren’t technical. Here’s the first:

Permalink: Trading Vs Investing

Trading is a business. Like a casino. You spread the risk over a bunch of tables and let the law of averages1 do its magic. Investing, whether it’s as a shareholder, LP, or creditor (ie allocating capital in the primary or secondary markets, but not as a member of management) is something you do in a business. You can invest in a casino. You can invest in a bank. You can invest in a trading business. The point is that investing and trading are actually different.

The distinction seems subtle because the language and mechanics of investing and trading overlap. Traders talk about diversifying as much as investors do. Restaurant owners don’t. Traders and investors both talk about position sizing. Software founders don’t. This makes it easy to confuse trading for investing but the former is a business, not an investment strategy. You would not compare Optiver, Jane Street, or SIG’s returns to a portfolio manager’s. Trading firms think in unit economics just like any business (“how many fractions of a cent of edge do I get per contract?”). The portfolio manager doesn’t have a similar analog. However, if we look at asset management, it collects fees. So if we zoom out, we are at the business-level of abstraction yet again.

There’s an interleaving of concepts that binds notions of “trading” to “investing” in a way that can mislead investors. When they trade are they trading like they are a business, like they are providing a service (temporary liquidity in exchange for a theoretical fee which resolves the desire for a buyer or seller to transact in the absence of a natural counterparty) or are they rebalancing investments? The distinction is one of framing and like all frames, it has a tyrannical grip on one’s downstream decisions. The subtlety can be confusing to new investors who can’t escape terms like “daytrading” or that Robinhood calls itself a “Stock Trading and Investing App”. You wouldn’t take a Porsche off-roading any more than you should confuse these 2 endeavors.

And yet you might for all the superficial similarities I already described. It’s totally understandable. To create the appropriate distance between activities of “trading” and “investing”, I’ll offer 2 thoughts.

  • Time Horizon

In trading, the bets have endpoints. Whether it’s an upcoming catalyst or event, an option expiration, or time to roll a future there is a time when you get to “see the river” to borrow a poker term. Price and reality must converge. Extrinsic values go to zero. Future prices meet spot prices. With equities, the metaphor needs massaging. Perhaps news or earnings is more like the “flop” or the “turn” whereas M&A activity serves as a defacto endpoint.

With investing, the duration of the trades is typically much longer. Stocks are perpetual claims. Perhaps semantically awkward, I prefer to re-brand investing as “re-investing”. This focuses us on a company’s need to compound returns on capital internally. If an oil company sits on massive reserves, but the price of oil shoots to a price that destroys all future demand, the stock would plummet because it no longer has a forthcoming stream of earnings. Yes, its book value would immediately increase, but that is a smaller portion of its discounted perpetuity value.

The “re-investing” frame explains why a market would discount such a one-time windfall. You can even think of a “cheap” stock as a company that the market has decided has a low future return on invested capital. By not increasing their bids, investors are manifesting trader thinking — they are focused on return per trial. Thinking of investments through the lens of how a company re-invests, stretches “repeated game” thinking longitudinally into the future as opposed to traders or casinos who think of edge per trade cross-sectionally.

  • Seeing The Present Clearly

Since the compounded return of an investment depends on how a company re-invests, it requires distant foresight into an inherently complex system. Long-term investing, like long-term weather forecasting has an irreducible bar of uncertainty that sits unpleasantly high off the ground. There’s only so much you can say about a system governed by chaos, biological, and evolutionary forces as opposed to tidy physical properties. Feedback loops are long, causation is opaque, and the signal-to-noise ratios are too low to prove an edge. This leads to a paradox. If a manager’s edge is unprovable, then there’s a chance you can actually access it, you’ll just understand it post-hoc. If the edge was provable, the manager would extract all the excess alpha for themselves by either choosing strategic investors or charging ransom fees.

Trading on the other hand is a provable edge. Because it’s a business. You rake a tournament, take the profits off the table and hunt for new players. Markets might imply or try to tell us something about the future. The business is to find market prices that say something contrary but have visibility to resolving and taking both bets. Arbitrage is an extreme example of this. If one person thinks the USA basketball is 90% to win the gold and another thinks the field is 15% to win the gold you can bet against them both and get paid $105 while knowing you’ll only owe $100.

The business process around this involves measurement, not prediction. There’s no thematic vision of what the world looks like 10, 20, 50 years hence. Instead, you find others who express strong opinions that disagree and build a machine that lets you bet against both of them. You are passionately agnostic. You are in the business of seeing today clearly. Not having visions of the future. That’s your customer’s job. That’s the investor’s job.

A Skinny Bridge

Coming from the trading world, I’ve wrestled with my understanding of investing. I don’t believe in crystal balls. I don’t think any “long term” investor can prove they are special because of the limits of data and sample size. Putting faith in track records feels like betting on coins that just had a long streak. There are a lot of funds out there, it’s inevitable some will have long streaks by chance. Survivorship bias makes the proportion of lucky funds even more visible.

This is a discouraging place to settle. Attempting to invest in a trading business as opposed to doing the trading business, leaves you in the same epistemological rut as choosing any business to buy. They are just businesses, to be compared with any other business. In fact, the search is pointless. Most are capacity constrained which means the best ones don’t need your money anyway. Where does that leave me? I don’t trust most people who would take my money to manage it and I don’t have the expertise to invest to the impossible standard of risk-reward that the business of trading anchored me to. And I need to take myself seriously — I just spent this entire essay explaining how it’s a fallacy to compare trading to investing in the first place.

Is there a reconciliation?

I think so. I see a skinny bridge between the business of trading and what it prescribes for investing. It lies in portfolio construction and asset allocation. At one level of abstraction, the investors with their coherent visions of the future are simply tourists in the traders’ casinos. But if we zoom out and aggregate the consensus of competing investors we end up with a total market price. It’s not one market however, it’s many. There are equities, bonds, and commodities. They exist across geography and sovereign systems. These are the legos that can be stacked to construct payoff shapes — carry, insurance, momentum. Those can be described in other language as well — concave/convex, convergent/divergent.

The asset classes themselves contain a risk premium above risk-free rates (by induction — stocks should earn more than t-bills because you need extra compensation to hold something that tanks every now and then). By combining these asset classes under battle-tested principles of risk management, the hope is to capture the weighted average risk premium of your allocation without relying on forecasts. Just like trading businesses. Just like casinos2.

Wrapping Up

Trading and investing are sufficiently different that you should be conscious of what mode you are in when you click a buy or sell button. The awareness will likely lead you to pressing buttons less often, or systematizing when you push the buttons. Unless you’re in it for the thrill, you want to minimize your points of contact with the fee-generating businesses that want you to feel like you are doing a good thing by “investing”. You are doing a good thing when you invest, but be careful — sometimes what looks like investing is trading. And the bar for doing that productively is much higher than they want you to believe.


Last Call

I’ll be in NYC this week for the StockSlam Sessions with Steiner and Tina.

Paul Millerd recently interviewed Steiner. My favorite thing about talking to Steiner is his experience and perspective on high school kids. It’s easy to focus on negativity, but Steiner teaches at a diverse public school in NJ and sees so much positivity and optimism in how the kids treat one another. I get it, that doesn’t get the clicks. The incentives aren’t really for truth so we shouldn’t be stunned when the happy news is more correct (this would actually make a neat Bayesian homework problem to make the point).

Steiner’s experience is anecdotal so I’m not generalizing. I’m just saying — this isn’t going to be negative, click it anyway:

Training Elite Wall Street Traders (podcast/video)

From Paul:

This conversation was a delight and I think you’ll enjoy it. We cover:

  • Ending up at Penn and not really knowing what he was going to do
  • Figuring out he enjoyed math and finance
  • Getting a job at SIG
  • Joining the training team
  • Leaving finance to spend more time with his kids
  • Becoming a high school teacher
  • How he thinks about teaching & mentorship
  • His 20-year journey in creating his game “Stockslam”

From My Actual Life

I’m going to the Greek in Berkeley tonight for the 3rd time in as many weeks. We are seeing the Aussie band King Gizzard and The Lizard Wizard. They are the most prolific band of the past decade. They release more than 1 album per year. Last month they dropped 3 albums. Not a typo. They have played over 100 different songs on their current tour and the range of music goes from metal, to pop, to spoken word. They are far out. The music videos are a trip too.

Funny thing about these tickets. I bought them a year ago thinking they were for 2021. I didn’t realize the date was off by a year until the morning of. And this worked out for the better because tonight’s a date night. Yinh and I are celebrating our 13-year wedding anniversary. We got married in Mexico and I remember the all-nighter she needed a few days before the flight to get this document to the printer in time to get into to the guests’ welcome bags:

Moontower #163

Lately, I’ve been watching Pirates of Finance episodes during my weekly cardio sessions. Jason and Corey are a special combination when they just riff on whatever pops in their head. A recent episode, The Gamification of People, provoked some musings.

Where Exactly Are We Racing To

The pirates revisit Malcolm Gladwell’s discovery that the best hockey players in Canada were disproportionally represented by athletes whose birthdays were just after the grade cutoff. So children who are the oldest in their class or hit puberty in their class first have an advantage.

If you are a summer birthday you understand this. The school year starts, and some student brings Rice Krispy treats for the class and you think “this mf is a whole year older than me”. Jason remarks that even though he has no kids, he has heard that parents in affluent suburbs hold their kids back at a young age so they can be swept up by the positive reinforcement loop of being a better athlete or student. A ”snowball effect” builds as a confident child draws more attention from coaches, gets into the higher track in class, and is even less likely to be diagnosed with ADHD.

Via WaPo:

Researchers found the youngest children in a grade — those born in August, just before the cutoff — were significantly more likely to be diagnosed with ADHD compared with those who were born the next month and became the oldest in their class.

Corey notes that as knowledge of Gladwell’s chapter in Outliers spread, the efficient market mechanism kicked in. Parents started holding their children back a grade. Jason, who admittedly has no kids, sounded skeptical. Jason, if I was in the comments section of the livecast, I would have told you — the practice is called “redshirting”. Like the NCAA athletes.

Our local school district is extremely strict about not allowing it. By making the date cut-off a redline, they don’t have to deal with every case-by-case plea to hold kids back. In fact this week, I was chatting to a mom of triplets at my kids’ school, who despite a totally valid reason (in my totally unqualified opinion) for holding the kids back, did not get an exception.

The impulse to redshirt your kid, even though you risk them being bored by playing “down” a level, for a competitive advantage is classic Moloch — a race to the bottom. If a parent doesn’t hold back their kid in such a community are they now doing them a disservice? I mean what a miserable question to entertain. But here we are.

A few years ago, schools in our area decided to move the scholastic calendar to start in early August. Why? So they can have more time in class to prepare for the end-of-year standardized state tests. What has been the cost of this intervention? Togetherness. My kids now go to school a full month earlier than their cousins in NJ. The end of August is a classic time for vacation with both camps and school out of session. I know, I know — violins. I won’t turn what amounts to a high-class problem into a crusade, but the point is the school is reaching for an artificial advantage. If every school adopts this calendar, the advantage goes away and we are just worse off. It’s all frustratingly familiar.

Let’s go back to Corey’s point about market efficiency. Mechanically speaking, he’s right. But it’s actually more interesting as a demonstration of the flaws in market-maximalist thinking. If you graduated from U of Chicago, turn back now. You’ve been warned.

The market is a servant of our collective values. If we choose the wrong values we are asking to be consumed by the “paper-clip maximizer”. This is exactly why AI research is so concerned with safety. We tell the system what to optimize for and it will do so faithfully — but without an appreciation for what we forget to tell it.

Market-based thinking needs to be accompanied by a responsible understanding of our values. This runs head-on into an accounting problem — “not everything that we measure matters, and not everything that matters can be measured”.

A specific instance of this is negative externalities. The textbook examples are companies that socialize the costs of pollution while capturing private profit. More oblique examples abound in Corey and Jason’s conversation. How does the UI of investment platforms “nudge” our behavior? Are those nudges good for the clients, the company, or both? They give the example of a robo-advisor that tells you the concrete tax cost of selling appreciated assets. It’s an effective speedbump because investors hate paying taxes. It seems like a win for both the advisor and client. But how do we compare the sure tax savings against the theoretical risk reduction that happens by cutting concentration? This is hardly straightforward. You don’t have to be THAT cynical to think that a tie goes to the robo-advisor’s interest. Would a more nuanced speedbump that considers the trade-offs of different actions fulfill fiduciary responsibility better? Is it worth the brain damage to clients?

I don’t have answers to any of this. One of my beliefs is that our dashboards of cost/benefit are woefully underpowered. Partially because of incentives — commercial interests talk their own book. But also because of irreducibly complicated chains of causation. Even if you could construct higher fidelity models of reality, internalize all the externalities, and identify the “best” values you’d still fail. Because on average people don’t really want the truth. We are cognitive misers. We either want the laziest solutions or we want to keep our delusions intact.

I’m pro-markets. But any platonic idea that they are “free” and not downstream from laws motivated by imperfect actors is an illusion. That markets do a generally effective job in allocating resources reminds me of that Twain bit: It ain’t what you don’t know that gets you into trouble. It’s what you know for sure that just ain’t so. Misplaced confidence is more dangerous than things we know are dangerous because things that appear safe become load-bearing. If a money-market account defaults, that is far scarier than BTC going to zero because we size our exposures in proportion to how safe they are.

We need to be careful about what values we ask markets to chase. Free market maxis love to cite the law of unintended consequences against nudgy top-down policy. That’s valid. But the sense that markets, whose guardrails emerge from human negotiation and therefore limited foresight, aren’t immune to unintended consequences is a fantasy.

No idealogy is so important that we can’t inquire — who’s serving who?

Ouija Boards

Corey and Jason struck another nerve. They get into the topic of sales. They acknowledge that while they have an idealistic aversion to sales, that’s not a practical position. Everything is sales because sales is persuasion. From getting clients to finding a mate. No controversy there.

Consider the used car dealer’s tactics — lying, creating urgency, and so on. Yes, it’s cringe, but…it’s also a strawman. The best salespeople don’t look like they are selling. And they often aren’t in the conventional sense. They aren’t trying to convert you, they just cater to your bias. That sounds nefarious but it doesn’t have to be. If I am in the market for an investment fund, tell me why I should want yours. I’m buying one either way, put your best foot forward. It’s hard to distinguish “talking your own book” from “the manager is employing strategy X because they believe in it”. They are already betting their career on it. Where does belief end, and conflicted interests begin? It’s a tough question. Sure, the benefit of a doubt needs to be earned but assuming everything is a scam will leave you in a cave.

Back to the tactics. The pirates mention “mirroring” and saying people’s names (“John Smith, let me tell you something about this car”) as examples of manipulation often found in sales guides or books like Cialdini’s Influence (brief notes from an interview with the author here). Corey acknowledges that some people do this naturally.

I felt seen.

If a server tells me their name, I use it. I tell myself this is a way to be kind. I take the Zeroth Commandment seriously. But am I post-rationalizing an adaptive behavior? Have I figured out that being kind is a way to get what I want? Am I manipulative?

I feel like I’m shooting airballs here because I just don’t f’n know. There are 2 kinds of people. Those that are full of shit and those that admit it. It’s a bit of a cope, but I’m old-fashioned in thinking intentions matter. It makes you sound smart to moan about the road to hell being paved with such intentions. It sounds smart because there’s truth to that. But it has less to do with intentions themselves and more to do with reality being sloppy spaghetti. The arrows of causality are far more bi-directional and recursive than our coherent explanations suggest. Well-intentioned people often come off looking like Steinbeck’s Lennie strangling the objects of their affection by not knowing any better.

Still, discounting intentions fully in deference to optimization is a cope of its own. Incentives are Oujia boards. They guide us to what we want while we tell ourselves stories about how our beliefs make sense. We spell out the letters of whatever serves us individually.

And then we look at one another “Did you move it? I wasn’t moving it. What does it spell?”

J-U-S-T-I-F-I-E-D


Today’s letter is brought to you by the team at Mutiny Fund:

How can you access a multi-asset strategy concerned with protecting assets and growing long-term wealth?

The Cockroach Strategy seeks to achieve higher long-term, compound growth compared to traditional stock/bond-focused portfolios with more limited drawdowns. ​ It is intended as a total portfolio, a ‘set it and forget it’ approach that strives to give investors peace of mind and meaningful capital appreciation.

The Cockroach strategy consists of a diversified ensemble of assets including stocks, bonds, commodity trend strategies, long volatility strategies, and gold. It is designed to perform across multiple macroeconomic environments: growth, recession, inflation and deflation.

The Cockroach strategy gives investors exposure to asset classes designed to perform in each of those environments including stocks, bonds, commodity trend strategies, long volatility strategies, and gold.

Click Here to Learn More

Disclaimer: Investing is risky, and you are reminded that futures, commodity trading, forex, volatility, options, derivatives, and other alternative investments are complex and carry a risk of substantial losses; and that there is no guarantee the strategy will perform as intended.


Money Angle

With the StockSlam Sessions rapidly approaching, I want to thank Jeff Malec at RCM Alternatives for inviting Tina, Steiner, and me to his show. You can listen to the pod or watch on Youtube. Steiner is an offline guy, so foremost this is a nice introduction to him.

  • The Game of Trading with SIG Alums Kris A, Tina L, & Steiner (Link)

    We have a little saying over here on The Derivative, “The More, The Merrier”, and on this week’s episode of The Derivative, we’re not chatting with one guest, but THREE! Class may no longer be in session, but we are taking a trip down the SIG/Susquehanna memory lane and having our own class reunion with Kris Abdelmessih, Michael Steiner, and Tina Lindstrom.

    If you’re interested in learning how big trading firms find and teach their traders, hold on to your seat because these three give you the answer key! Kris, Tina, and Michael are in session with Jeff and discussing competing with peers, finding an option’s fair value, making markets, and being in the game of trading, educating kids with board games, and of course Steiner’s new trading board game: Stock Slam! Discover how the game works and how you can join up with these three in NYC for a live session in this three-of-a-kind episode

We are doing these sessions because trading is a neat laboratory to learn about decision-making. Weighing risk-reward, thinking adversarially (this thread by @0xDoug is in my hall of fame), resisting confirmation/hindsight biases, using probability, considering counterfactuals, not “resulting”, and much more. So much of my writing focuses on these “meta” topics because trading gave me a better education than school ever did.

If we can help people practice thinking this way, it’s a like growing new brain lobe that’s adaptive for many real-life situations.

The following is adapted from a thread I wrote that demonstrates an idea in a trading context:

People understand that even though insurance has negative expectancy it can still improve a portfolio that is focused on compounded returns. It makes no sense to look at the line-item of insurance divorced from the optionality it gives you in the rest of your portfolio.

(I could pull lots of links on this idea, but let’s be brief).

This concept is fractal. Let’s zoom in on the smallest portfolio — a spread. You don’t necessarily care about the p/l of any individual leg of a spread trade but the performance of the spread overall.

Before we consider a spread, let’s just look at the single position. Suppose you buy something for $4 when it’s worth $5 but then sell it for $4.50. You made both a:

  • +$1 expected value trade
  • -$.50 EV trade.

If you knew it was worth $5 you negated half a good trade with a bad trade.

In real life, you often might like the price of a spread but it’s hard to tell which leg is the “good side”. That’s one of the reasons you trade the spread. Once you do the spread you don’t care about the individual p/ls.

Another reason you may do a spread is that you might like a trade (ie maybe vol is cheap in X) but can do it bigger if you spread it. This is one of those questions that comes up a lot on real trading desks. Do I like the outright, or do I like the trade better paired against something else (and assuming I can do the trade bigger if I spread it)? Do I like being long z units of X exposure, or do I prefer 5z units of (X-Y)? The answer depends on understanding the distribution of the outright vs the spread and the relative price of each within those distributions.

Finally, there’s the general lens of how I approach trading (which I discuss in the RCM interview). Liquid markets tell us a lot about “fair value”. If we take fair value as the consensus “outside view”, then we can examine illiquid markets for pricing discrepancies compared to that outside view. Of course, those markets have their own idiosyncracies, so you need to take an “inside view” and normalize as much as possible to the liquid reference asset. This is a standard way to identify possible opportunities. It’s a mix of art and science. The science is in the measurement but the art is in handicapping how much the differences should matter. This isn’t arbitrage. It’s informed betting. If you need certainty, you will either be too late or the strategy will have the lifespan of a mayfly.

[I actually googled “shortest lifespan” and was met with irony:

We often hear that mayflies, like the whiteflies of the Susquehanna River, have the shortest lifespan of any animal on Earth, just 24 hours for many species.

SIG is named after that river.]

Now let’s broaden the concept to investing. For that, I turn to Byrne Hobart’s paywalled post Assuming Efficient Markets to Exploit Market Inefficiencies:

If there’s an efficient market A and an inefficient one B, A is easier to trade in, but B is probably the one that’s mispriced. So that price inefficiency partly represents a measure of how hard inefficiencies are to exploit! In the case of Druckenmiller’s recession call, he actually made the paradoxical judgment that inefficient market B was priced incorrectly relative to A, but that A was the one to bet on—because the specific inefficiency at hand was that a recession was likely and it wasn’t being accurately reflected by anything.

This raises an important point, because there are two broad ways to look at relative inefficiency. One is to just stick with the relative argument: if stocks are pricing a boom and bonds are pricing a recession, bet that one of these will go away. But that’s a frustrating conclusion to draw, because it basically amounts to saying: The market is telling me something important, and I don’t care what it is. The relative-value bet works equally well regardless of which thesis is right, but it’s still outsourcing a lot of judgment to the market. And annoyingly, once the valuation gap closes, you have two problems: first, you haven’t figured out why the discrepancy existed in the first place, and if there’s an inexplicable 1-standard deviation change in some correlation, there is no law of the universe saying it can’t go to 2 or 3. (There is a weaker law saying it can go to 20, when enough levered participants are betting on it.) The other problem is that real-world theses produce additional ideas; an argument that the economy is going into a recession has second- and third-order consequences, and generates more ideas.

This kind of tradeoff, between a low-risk claim that two views are contradictory and a higher-risk claim that one of them is right, extends far beyond finance.

Through games, direct instruction, and making connections between abstract concepts and examples in the wild, Tina, Steiner and I want to see if we can help others get better. And selfishly, I want to think better, so I’m stoked to be a part of this.

*Applications are closed and invitations already went out but these sessions are an experiment to guide how we test and improve the transfer of knowledge. If you didn’t get accepted it’s because space was extremely limited compared to applicants. This is not meant to be exclusive, we are going to figure out how we can spread what we learn. As Axl once said, we just need a little patience [bandana sway].


Last Call

A friend recently mentioned that she willfully puts on blinders about big questions. She prefers to focus on the practical because it can be painful or lonely to dwell on the large problems we see in society.

I’m sympathetic to this view. It brings me to a conclusion I’ve come to over the last few months. You can’t tear down people’s constructs without offering another way. It’s a riff on “the best way to complain is to build.” If you succeed in providing people an alternative the old will crumble away on its own. You don’t blow up someone’s house without having a better one waiting for them. With a bow on it.

It’s the same reason you wouldn’t tell young kids you can’t pay the rent. They can’t do anything about it. Being around Steiner again has been inspiring because he really understands this. Steiner doesn’t criticize unless he has a solution. He can lament, but won’t pontificate. He recognizes that whining without proposing thoughtful solutions is not just annoying, it’s intellectually lazy.


From My Actual Life

Kids are funny.

Moontower #162

The paradox is that you write to become more fully yourself, but then you find it hard to live with the self you’ve become. I do what I can to remain a possibility instead of a reality. Thus the flow. And, next week, the effort to erase this too.

-Freddie deBoer on why he feels the need to write frequently. I don’t think you need to be a writer to appreciate that feeling.


Friends,

I’ve got this friend and neighbor who I hike walk with after we drop the kids off at school sometimes. It’s like 90 minutes of dorm-room musings befitting of the Moontower scene. Those conversations have influenced a few of these weekly letters.

This recent one was no different. It got me thinking about diversity.

See, this friend has an early-stage startup in the education space. The internal research at his company parses diversity across many dimensions. You are familiar with the capital “D” types of diversity — race, religion, gender, age, sexual orientation, socioeconomic, etc.

Interestingly, he expressed concern that his team might not be diverse enough. Not in a visible way. The team runs the gamut of the capital “D” diversity categories. But he was interested in cognitive diversity. He was concerned that an intellectual echo chamber of fancy-college liberals could lead to blind spots in their collective decision-making.

Now I don’t have much team-building experience. So I flexed some knowledge I recently read. (This is why people read right? To at least have a tennis racket when they find themselves on the court of conversational Wimbledon.) And now you too shall witness the fact that I read a book. Confer prestige heavily and without reservation, my esteemed landsmen.

Nah, really I actually read a book and it said some cool stuff. I’ll get to that in a sec. First, I want to re-surface some points professor Mauboussin made about cognitive diversity. He described it as the training, experience, and personality that make an individual unique.

He writes:

I think one can make the case very seriously and quite rigorously that social category diversity contributes to cognitive diversity, but it is cognitive diversity that we’re after.

He describes a less-talked-about form of diversity as well.

“Values diversity”. You might think about it as a sense of purpose, and on that, you actually want to be low. We want a common mission, even if we are of very different backgrounds, we’re pulling in the same direction.

In other words, my friend’s instincts about diversity are correct. Visible diversity is an imperfect proxy for intellectual diversity.

Back to the book I was reading — Superforecasting by Phil Tetlock and Dan Gardner. The book’s main thesis, which falls out of the lessons from the Good Judgement Project, is that it’s possible to become a well-calibrated forecaster in complex (but not all complex) domains. How good can you become? The best are able to consistently beat prediction markets, something even demonstrably above-average forecasters struggle to do.

This is rightly provocative because markets are effective truth-finding mechanisms. They are an ancient way of coordinating human behavior (democracy is another example of a human-coordination machine…for a contrast between markets and democracy see Dinosaur Markets).

If you read this letter regularly you know I have a lot of respect for the efficiency of markets. It’s not a strong-form academic belief. It’s more of an informal razor: “my null hypothesis is there’s no easy money and the burden of proof is on investors who think otherwise”. The academic compromise is markets are “efficiently inefficient”, reflecting the idea that there’s a cost associated with finding inefficiencies so some amount of inefficiency always exists to justify the hurdle of hunting for it.

To appreciate why markets, under certain conditions, triangulate on the truth, I paraphrase Tetlock’s explanation of how the “wisdom of crowds” works:

Bits of useful and useless information are distributed throughout a crowd. The useful information all points to a reasonably accurate consensus while the useless information sometimes overshoots and sometime undershoots but critically…cancels out.

The Role Of Diversity In Truth-Finding

The “under certain conditions” is an important asterisk. The expression “wisdom of crowds” is actually a modern idea that plays off the “madness of crowds”, a term coined nearly 200 years ago by journalist Charles Mackay. For the crowd to generate wisdom, it needs diversity. In other words, the errors in judgment need to be uncorrelated to cancel out.

In Tetlock’s studies, they tested the forecasting abilities of individuals. They were rigorous in their experimental design. They were curious how teams of forecasters would perform against individuals. They further experimented with the composition of those teams.

The eye-opening results underscore the importance of diverse thinking:

  • Teams are more effective
    • The results were clear-cut each year. Teams of ordinary forecasters beat the wisdom of the crowd by about 10%. Prediction markets beat ordinary teams by about 20%. And superteams beat prediction markets by 15% to 30%.
    • “Emergence”: teams are more than the sum of their parts. This cuts both ways…even actively open-minded individuals could surrender to “groupthink”
  • “Diversity trumps ability”
    • This provocative claim highlights how the aggregation of different perspectives can improve judgment. The key to diversity was, unsurprisingly, cognitive diversity.
      • The revealing result: When they constructed the superteams they optimized for ability and those teams happened to be highly diverse because the superforecasters themselves were highly diverse. They did not optimize for diversity first, but it turned out the most diverse teams were the most effective.
  • The asymmetry of the extremizing algorithm
    • The “extremizing algorithm” is a technique where you boost a 70% prediction closer to the extreme, perhaps bumping it to 85%. It’s a technique that is employed when the forecasters have diverse perspectives because it leads to better-calibrated forecasts.

      You do the opposite (push the forecast probability closer to 50%) to combat “groupthink” if the team is comprised of people who think the same or possess similar knowledge. (The use of the extremizing algo allowed teams of regular forecasters to actually perform better than some superteams!).

      My own observation: this is the same logic by which correlated observations “shrink” the sample size, an idea familiar to data analysts.

Example Of Cognitive Diversity

My friend with the start-up gets it. He is concerned that the visible diversity on his team might be a poor proxy for what he really wants — cognitive diversity. If you are an oil company you need geologists, finance people, managers, political connections, real estate expertise. This is a clear example of needing to pull together many object-level competencies.

But cognitive diversity is not just “what do they think about”, but “how do they think”. For an example of what I call meta-cognitive diversity, Tetlock uses the “hedgehog” vs “fox” duality. As a pre-defense of Tetlock, he warns about overstating this dichotomy. (He exemplifies non-binary thinking throughout the book, doing an honest and eloquent job of pointing out tensions and caveats, not unlike the superforecasters themselves).

I’ll take a stab at describing hedgehogs and foxes:

  • Hedgehogs

    Hedgehogs are specialists. The 10,000 hours crowd. The natural endpoint for the logic of economic comparative advantage or simply the rightful throne of the devoted craftsman. The “specialization is for insects” objection is too reductive. We are better off when Eddie Van Halen wants nothing else than to just be Eddie Van Halen.

    But there are trade-offs. Hedgehogs often filter observations through the lens of their expertise. (My online friends have a good-natured running joke that I see everything as an option — classic “when all you have is a hammer, everything is a nail” thinking). But a camera lens’ usefulness depends on the context. Sometimes that fisheye or telephoto lens is exactly the wrong tool for the job.

    This is inconvenient for the status-aware hedgehog whose incentive to remain consequential leads to motivated reasoning and self-delusion. Academic researchers who become famous for writing about an idea that catches fire have a lot to protect. They become fast friends with Mssr. Confirmation Bias and Madame Overconfidence, the very enemies they used to fight when they were building their reputations of good work. It’s like America fighting against the same Afghans they armed as rebels in the 80s. As DiCaprio’s character in Up In The Air would attest, the warm embrace of fame beats the cold loneliness of cultural anonymity.

  • Foxes

    Foxes are generalists. Businesspeople, investors, politicians, administrators. It’s an imperfect description of course but you know the type. The disadvantages of being an “inch deep and a mile wide” are established. That person is never going to design a bridge or coach a professional sports team. Some are self-aware enough to recognize when they “know enough to be dangerous”. Many are not. Their advantage, however, is their mercenary relationships with lenses. The ego cost of finding the most useful lens is much lower, making foxes at least psychologically fit for reasoning across domains.

Remaining careful not to play into false binaries, the hedghog/fox continuum reminds me of the importance of shifting between diffuse and focused thinking modes. Diffuse thinking (see More Shower Thoughts Please) provides both inspiration and the ability “see over the neighbor’s fence” while focused thinking enables us to synthesize those scattered insights into a useful output. Most of my posts start either in the shower or when I’m taking a walk. (I strongly recommend this old New Yorker piece Why Walking Helps Us Think). “How we think” is a dimension of diversity.

The Complicated Discourse Around Diversity Is Inevitable

When I described the thrust of this piece to my wife, Yinh, she yawned. “So you’re writing a post saying ‘diversity is good’? Who is this news to?”

I immediately got nervous that I was belaboring an obvious point. I asked her why she thought it was so obvious and she started citing studies and initiatives that could easily have 10x’d the length of this post.

Now I can take feedback, but I’m not above quibbling en route to my final destination. So let me get this straight. You read a bunch of stuff arguing that diversity is good, now it’s obvious to you and presumably everyone else who reads, so I shouldn’t spend any time making arguments that diversity is good. I mean, this post is to a Moontower reader as that other research was to you. Next time just put my head in the washing machine woman.

But she still has a point. Diversity, in its many forms, is widely celebrated. In-breeding is taboo. I was just watching the National Parks series on Netflix with the kids and learned that rainforests, the most biologically diverse ecology on land, are the origin of more than 25% of modern medicines. So why do I feel the need to cheerlead an “obvious” point?

The short answer is I don’t think the case is closed on the merit of diversity. I know it’s exhausting to hear me say this, but it depends on contexts. For example, whenever America’s dysfunction is compared to a homogeneous European country, I scratch my head. If we are tribal in nature, our default wiring might simply make governing a melting pot inherently more difficult. I think diversity makes us stronger overall, but some measures of local harmony should expect to suffer. I’m even open to the possibility that tolerance runs counter to our natural instincts. (It just makes a normative approach to overriding our base impulses require extra care. Law-making is always a tug-of-war between collective values and the animals within us.) In other words, I can appreciate how diversity can be a headwind.

But there’s more.

Even if we wave a wand and agree that diversity is an unalloyed good, there remains the harder question. At what cost? The lightning rod version of this question is you have a white student and black student who look the same in all other ways and you need to choose one (the premise is unrealistic, but this is the collapsed version of how these questions get passed around the media and people extrapolate entire political identities on how they’d answer such a fake question). If everything else is the same and there is a non-zero probability that social diversity leads to cognitive diversity, then the optimal (although not necessarily morally fair which is a different criteria battleground) decision gate would say select the black kid (assuming the majority of the student body were white).

Still, even if we agreed on that, a harder question remains. What if the black kid had a slightly worse score on a standardized test? From a strictly efficient-utilitarian point of view (again, moral consideration aside), then we are faced with trade-off on a diversity-competence frontier. In a purely academic sense, I was likely an inferior hire at SIG, but perhaps something about how I thought or acted might have made my “diversity” or “complementariness” worth more than just hiring yet another 1600 Math SAT kid from MIT (or they just exhausted the supply of those, I’m not trying to flatter myself here). The point is that the merit of diversity is fairly intuitive, but doesn’t lend itself to legible number-crunching in the way test scores do.

Pricing “diversity” could very well be a fool’s errand. But I have one final bit of intuition to sprinkle on the problem. In There’s Gold In Them Thar Tails: Part 2I rehash how nature uses diversity as fuel for evolution.

  1. Diversity is an essential input to progress. Nature’s underlying algorithm of evolution penalizes in-breeding.
  2. In addition to a loss of diversity, signals decay as you get closer to the extremes. This is known as tail divergence. The signal can even flip (ie Berkson’s Paradox).
  3. The point where the signal noise overwhelms the variance in the candidates is an efficient cutoff. Beyond that threshold, selectors should think more creatively than “just raise the bar”.

At some point, incremental diversity is worth more than incremental “signal”. Evolution acts like a basket of options (I really am a hedgehog). It sees a mutation. If it’s useless, discard. If it’s adaptive, exercise it and let it multiply through the population out-competing those without the adaptation. When discernment becomes random, select for diversity. The downside is limited, the upside is massive learning.

Wrapping Up

Diversity is valuable. The word is highly politicized today. There are many arguments, with varying degrees of merit, harping on diversity in the name of fairness. Those are debates that need to be had. But this is not that debate. This has been an argument that diversity is important as a matter of efficiency and flourishing. Perhaps the argument isn’t needed, but I suspect that many reactionary arguments against the equity angles of diversity may dilute the value of diversity as a general concept.

We have seen diverse dimensions all around us: social, cognitive, and values themselves. It’s worth unloading the hangups artificially narrowing the meaning of a beautiful word — “diverse”.


Today’s letter is brought to you by the team at Mutiny Fund:

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The Cockroach Strategy seeks to achieve higher long-term, compound growth compared to traditional stock/bond-focused portfolios with more limited drawdowns. ​ It is intended as a total portfolio, a ‘set it and forget it’ approach that strives to give investors peace of mind and meaningful capital appreciation.

The Cockroach strategy consists of a diversified ensemble of assets including stocks, bonds, commodity trend strategies, long volatility strategies, and gold. It is designed to perform across multiple macroeconomic environments: growth, recession, inflation and deflation.

The Cockroach strategy gives investors exposure to asset classes designed to perform in each of those environments including stocks, bonds, commodity trend strategies, long volatility strategies, and gold.

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Disclaimer: Investing is risky, and you are reminded that futures, commodity trading, forex, volatility, options, derivatives, and other alternative investments are complex and carry a risk of substantial losses; and that there is no guarantee the strategy will perform as intended.


Money Angle

I’m trying to read books again. I’m like the opposite of a junkie. I start and just give up. I struggle to watch movies for similar reasons. It’s hard for me to sit still and be passively entertained for extended periods of time.

[I recently admit that I haven’t seen Animal House, I saw Trading Places after I had been a trader for a decade, I saw Caddyshack 2 years ago. I’d like to claim ESL but I was born in Brooklyn. Also I’d be doing a disservice to immigrants, many of whom have large movie repertoires because it’s an effective way to learn English. I have no excuse. I could have watched more classic movies instead of fraying the tape of the Dazed And Confused VHS.]

In an era of amazing tv shows, my diet mostly consists of those that come in 30-minute episodes. I’m making my way through all the seasons of Curb Your Enthusiasm again. I’m also watching it backwards. For example, when season 3 ended, I go to Season 2, episode 1. This isn’t the first time I admit to being a serial killer. Pun intended.

Back to books. To get my groove back, I committed to reading 1 chapter a day. It worked. The streak is intact and I got to cross a title off the list that I’ve wanted to read for a long time: Superforecasting — The Art And Science Of Prediction by Phil Tetlock and Dan Gardner.

I really enjoyed this book and would consider it canon for aspiring analysts and traders. You can find my notes below. Here are the high-level takeaways:

  • The world is complex (a butterfly flaps its wings and small change in initial conditions leads to disproportionate outputs). So our ability to forecast is existentially limited.
  • But some people are demonstrably better forecasters and it’s not just luck. They are consistent.
  • Those people are not geniuses. But they have a mix of qualities and procedures that enable them to forecast at a high level.
  • The key to getting better, same as in sports, is useful feedback and iteration. It takes hard work, “deliberate practice” and a commitment to get better.
  • Getting better is necessarily a conscious, painstaking process because our natural biases conspire against our judgment in areas where causality is opaque. Which are most questions of interest.
  • How groups can hinder or improve forecasting. The role of diversity in group decision making.
  • In many contexts, making accurate predictions is actually undesirable. Regrettably, I want to shout Moloch everywhere I look. The expression to look for in the notes: “kto, kogo?” It’s a disheartening idea.
  • The leader’s dilemma: balancing decisiveness in the face of uncertainty and intellectual humility
  • Objections, progress, and goals in the endeavor of forecasting

    Continue to…

    Notes On Superforecasting (Moontower Book Guides)


Last chance to apply to the free StockSlam workshops I’ll be hosting with Tina and Steiner in NYC the first week of October.

Details and application:

Last Call

A year ago, I talked about seeing comedian Sheng Weng at the Punchline in SF:

His powers of observation on the mundane details of daily life are Seinfeldian. His signature tone and voice deliver self-skewers that you can’t help but turn on yourself.

One of our friends said it was the hardest she can remember laughing for so long. Sheng’s a craftsman and the more you listen to him the better it gets.

He’s actually Yinh’s college friend (they bonded over their rhyming one-syllable Asian first/last name combos). This spring we were supposed to go down to LA to see the taping of his Netflix special (Ali Wong produced it) with my friend Khe and his wife. We had to audible at the last second and missed it, but…it’s finally out!

Check out Sweet & Juicy (Netflix)


Speaking of Khe, he has been a most generous sherpa to so many people trying to raise their productivity game. He’s an alien jedi.

Check out his upcoming bootcamp. Oh yea, it’s totally free.

If you are curious at all as to why I’m always touting Khe and his community, do it.

Sign Up For The Free Bootcamp

The $10K Bootcamp is a free 3-day event hosted by Khe Hy from RadReads. During this free event, we’ll teach you how to design a system to achieve your goals (while working waaay less). You’ll learn how to:

  • Stay focused on the most important things in life
  • Think bigger (versus making smaller things better)
  • Stop putting things off until some imaginary future date
  • Invest in improving your mind, career and relationships

Event Details:


From My Actual Life

I saw Nine Inch Nails last Sunday night at the Greek in Berkeley. (Between Leon Bridges last week and the upcoming King Gizzard and The Lizard Wizard show I think I’m asking to be swallowed by the Earth. The Hayward fault runs beneath Cal’s football stadium and the theater. At least I’ll be in my happy place when the worms eat me).

I never owned a NIN album but since I’m alive I know like 6 or 7 songs. Any preoccupation I’ve ever had with Trent Reznor revolved around him renting 10050 Cielo Drive in the Hollywood Hills — the home where the Manson apostles murdered Sharon Tate and her celebrity friends. The recording studio in the house was called “Le Pig”, a reference to a song on the Beatles’ White Album from which Charles Manson inferred a lot of craziness. The killers smeared the word “pig” in blood on the home’s front door. Downward Spiral and Broken were both recorded at Le Pig. The music video for Gave Up features images of the house and studio. (Not to be extra creepy after I already used the word “serial killer” once in this letter, but the house I used to own here in CA looked similar to that infamous abode before we renovated it).

But I must admit. NIN is in the running for best show I’ve ever seen (n of roughly 200). The gulf between the recorded & live experience is indescribable.

The Greek felt like a rave at a temple. In black t-shirts.

Moontower #161

I learned a new term.

“To Go On Account”

A pleasant term used by pirates to describe the act of turning pirate. The basic idea was that a pirate was more “free lance” and thus was, more or less, going into business for himself. — The Pirate Glossary

It applies to several parts of today’s letter. Oh and don’t miss the special announcement at the end.


Friends,

Last week, I shared the Engine Model. It was a blueprint for designing an integrated life. I paused my regular workflow to write that post for myself as my trip transitions from a three-lane expressway of exploration to a local 2-lane highway. I like doing meta-writeups like that for the same reason I like reading others’ frameworks…it’s a form of “trail magic”.

Via thetrek:

The term “trail magic” was coined by long-distance hikers to describe an unexpected occurrence that lifts a hiker’s spirits and inspires awe or gratitude. “Trail magic” may be as simple as being offered a candy bar by a passing hiker or spotting an elusive species of wildlife.

For those on a similar journey, or see a similar juncture in their future, I hope the post can at least provoke if not be practical. One area I wish it was more practical, was on monetization. That’s a tough topic, so let me back up.

Reputation is the longest-duration asset you have. [The great grift of 2021 will forever be trapped in the amber of my mind as the moment a bunch of business-famous influencers decided the bid to sell their reputations was juicy enough to finally smack. It was a calculated bet on the shortness of your memory.] If you are not a sociopath, your ethical boundaries extend beyond the borders drawn by law. But the law alone seems to fence some people in just barely. Oh my god, fan me now. Watching literal lawmakers insider trade is an act of contortion so lithe it allows them to limbo even under that low bar.

[Collecting myself.]

Where was I? Oh yes, being an f’n normal human. So in that post I didn’t wade into specific monetization models because I don’t know much about them.

Instead, I address them in principle:

Once you begin thinking of your work as an engine, as self-integration, and not a single bilateral transaction with one employer (or overlord if you are especially cranky about your choices) you have replaced an existential problem, namely the rejection of over-compartmentalization, with a technical problem. The technical problem is “how do I sustain such a life?”

This is new to me and I’m learning on the fly so I’m not the best guide here. But I can offer my philosophical perspective, knowing that it will likely evolve with experience. I still think it’s important to lay out principles as a tether to your values as you head out into the unknown. 

  1. Extract less value than you create

    This is obvious. Strip-mining is not a renewable strategy. I’d rather underpromise and overdeliver. This isn’t altruism, it’s good business. If you leave the high-pressure race, you have chosen to focus on the long-term. The advantage is you can use a different playbook that relies more on compounding which pays off with time, instead of quick, but hard-to-repeat scores.

    From Working For Free:

    In business, I always enjoy the Costco example. Charlie Munger has written:

    “When other companies find ways to save money, they turn it into profit. [Costco] passes it on to customers. It’s almost a religious duty. [They] sacrifice short-term profits for long-term success”.

    It’s not as hokey as it sounds. Think of it this way. They are hiding profits in the customer’s own pockets. They will be return customers. That profit is hidden from competitors’ wandering eyes and the IRS. The strategy commits Costco to keeping the customers happy because the profit is realized over the long-term. It’s simple but requires rare discipline.

    The profit that “sits in your client’s pockets” has a bookkeeping entry called “trust”. The fact that it doesn’t capitalize as an asset on your personal balance sheet is a shortcoming of accounting. You can’t let it fool you from the reality that you have stored your future income with your clients and in their word of mouth.

  2. Price your attention carefully

    When you consider a project, you must decide how much to charge. If the project requires diesel fuel and you are a sports car, it might not run or it might be inefficient. This feels like a one-off transaction. You should probably quote a “go-away” price. At some price, you’ll suck it up. But this should be rare.

    You want projects that have recyclable exhaust. If you suspect the exhaust is especially powerful, maybe you charge less. The point is to price your time or effort holistically. What is the first and second-order cost/benefit of taking on a particular project?

    An example of holistic thinking: I don’t paywall my letter because the loss of subs would cut off a valuable inbound fuel source. The cash would not be worth it. Instead, I reframe the forgone income as “marketing cap-ex”.

I don’t know much about monetizing an integrated body of work. I’m not especially commercial-minded. But I have friends that are further ahead on this path that I can lean on. In thinking about creating your engine, realize you are not alone.

Identify your own principles. It’s a way to stay “green” as you experiment with sustainable business models that empower you to stay on the path.

Sponsorship

In the past year, I’ve been approached by companies that want to sponsor this letter. Extra cash would make it easier to justify doing stuff like hiring a designer. I have some fairly irreverent ideas for Moontower swag that would be decidedly, umm, [lowers voice] befitting of the namesake?

So I was open to the idea. Especially since I will never paywall this letter. The only issue was most of the potential sponsors didn’t get me too excited. And the higher their bid, the less exciting they are. Go bumhunt somewhere else.

When I write to “find the others” I mean it. You make this effort worth it for me. You see, if I had to pick a single external metric to grade the body of work I’ve been calling Moontower, it would be the quality of its subs. By quality, I mean thoughtful people who care about getting better as co-passengers on this ferris wheel.

Out of respect to both you and me, I’ve been guarded about who I’d let get mindshare here. While I haven’t done a formal survey (I’m working on one though), I can tell this readership is smart and has many ultra-successful people within it. Almost all of you want to invest better and live better. You’re a pretty dream demographic to marketers. Fortunately, instead of me wrestling with which sponsors to match with, the answer landed in my lap.

My friends Jason Buck and Taylor Pearson asked me to sponsor the letter. They manage a fund of funds that comes from the “all-weather” style of investing. Many of you are familiar with that term because of Ray Dalio, but Bridgewater is to Kleenex as all-weather is to “permanent portfolios”. I have been invested in Jason and Taylor’s fund for nearly a year and I’m doing my own research now on how to be more hands-on transitioning my own portfolio to be more “permanent” 1.  The exhaust of this research will be making its way into these letters so we can learn together.

In addition to the sponsorship and in keeping with my desire to keep this totally inclusive to everyone I have added the ability to be a patron of Moontower.

If you hit this button you will see the choices.

If you pay you don’t get any special posts, but if there were interest amongst patrons for higher levels of 2-way interaction I’d be happy to explore that.

There’s no pressure. It’s not like tipping in U.S. restaurants where it’s expected because servers don’t make a serious wage. I pay for about 20% of the publications I sub to. And it’s never about “is it worth it?” for me. It’s just, “do I want to support this?” I turned the feature on this week and there is seriously zero pressure. I already get a lot from your attention.

[For the more accounting curious…since I’m not a W2 employee and I incur expenses to run these sites and have a home office, any income I receive up until my costs are recouped is like an untaxed dollar. We aren’t talking real money, but eventually, I expect to have built a biz where I re-purpose a portfolio of solutions to my own problems so that it solves other people’s problems too. So these moves can be seen as practice with live rounds.]

By the way, a quick shout-out to my first paying sub, Max S., who signed up shortly after I turned that feature on. As soon as I get some swag made, I’ll be asking for your address man!


Today’s letter is brought to you by the team at Mutiny Fund:

How can you access a multi-asset strategy concerned with protecting assets and growing long-term wealth?

The Cockroach Strategy seeks to achieve superior long-term, compound growth compared to traditional stock/bond-focused portfolios with more limited drawdowns. ​ It is intended as a total portfolio, a ‘set it and forget it’ approach that strives to give investors peace of mind and meaningful appreciation.

The Cockroach strategy is designed with the view that all economic periods can be categorized within the four regimes of growth, recession, inflation and deflation.

The Cockroach strategy gives investors exposure to asset classes designed to perform in each of those environments including stocks, bonds, commodity trend strategies, long volatility strategies, and gold.

Click Here to Learn More

Disclaimer: Investing is risky, and you are reminded that futures, commodity trading, forex, volatility, options, derivatives, and other alternative investments are complex and carry a risk of substantial losses; and that there is no guarantee the strategy will perform as intended. 


Money Angle

I feel lucky that Jason Buck reached out to sponsor the letter because I love what he’s doing (Yinh and I were early investors in their latest fund). In addition to managing a fund, Jason is co-host of what I think is the most underrated show on investing YouTube, Pirates of Finance.

In season 3, Jason and Corey Hoffstein changed the format so that there is zero preparation. The conversation is totally off the cuff. And it totally slaps.

It is free, buried booty that our theoretical economist says can’t exist because of efficient markets. But it exists. I’ll prove it by digging up 3 themes from their amazing recent episode Decision-Making Under Uncertainty and mix them with my own thoughts. We’re blending Moontower and Pirate rum up in here today.

Why ETFs Might Be Unsuitable For Some Strategies

ETFs are liquid structures designed to faithfully track NAVs (“net asset values”) because the arbitrage mechanism is outsourced by the issuer to an Authorized Participant. These AP’s are a subset of the market-making community.

The Pirates wonder:

Is the ETF structure, whose allure is transparency, the correct home for opaque, illiquid, or bi-lateral (ie there’s credit risk in the basket) instruments such as inflation swaps? What about semi-liquid holdings like corporate bonds or even TIPs?

The answer to such questions partially rests on the liquidity of the underlying holdings. Consider a question they allude to but I’ll make explicit:

If you hold long option or long convex positions via ETFs (or for that matter directly) will you be able to monetize them when they pay off?

This is a real and highly underrated concern. Bid/ask spreads are positively correlated with volatility. So how useful is it if the paper profit on a convex position can’t be crystallized because the bid-ask is wider than the parted Red Sea?

Suppose you buy a way OTM put option for $1. It explodes to $20 but the bid-ask is now $16-$24. Sure, you can sell it for a 16x return, but when that option was originally valued for $1, the pricing incorporated the idea that in some rare states of the world the option is worth $20. If you can never realize that $20, then you entered into a pretty negative expected value situation when you paid $1 for it in the first place.

Trading is hard enough, you can’t afford to not maximize small edges. In a separate interview Corey talks to option trader Darrin Johnson.

I paraphrase Darrin:

When you sell tails, you need to capture the entire premium. The hit ratio of selling tails is high but when you lose you lose many multiples of the premium. If you fail to collect the full premium, it will not make up for the losing trades. The difficulty of selling tails is even trickier yet.

Darrin explains how betting against longshots leaves you uncertain if you have an edge in the first place. In my words: good luck differentiating between a 50-1 shot vs a 100-1 shot. That’s the difference of 1 probability point but it’s massive in payoff space. [I discuss that idea further in Tails Explained.]

When volatility increases, transaction costs go up for everyone. Since market-makers are part of “everyone” then the cost of their own hedging (ie replication) goes up as well, so they charge wider-bid ask spreads to keep them whole. MMs represent the marginal supply of liquidity so can they pass the transaction costs of their own “COGs” to those demanding liquidity. We know the house wins both ways, but the house edge itself is correlated to what markets are doing. If the house’s margins above their “COGs” expand in times of stress, you need to haircut the expected risk mitigation from defensive positions. That cost will show up when you try to roll or monetize.

There are cases where that bookie’s vig will not be too punitive even in a volatile market. For example, if the option you buy is now so far ITM that it no longer has meaningful extrinsic value, then you can simply trade the underlying to monetize (although re-hedging will put you face-to-face with the market-makers again).

This brings us to the next theme.

Destination vs Path

If you have a view about the expected return of an asset in 5 years should you care about the path? Depends who you ask. Anyone marked-to-market (HFs, market-makers, futures traders) will say yes especially if they are managing money for others. PE, RE, and bond investors are more likely to say no. The Pirates have a nuanced discussion about whether it’s even possible to manage to path versus manage to terminal value.

I’m biased by my path-or-die experience in trading. Mark-to-market is the goddess of tomorrow, you can’t afford to piss her off.

Here are a collection of arguments that I offer her as tribute.

  1. Bond investors who ignore path are fooling themselves.

    In Why Volatility Still Matters To Buy-And-Hold Investors, I summarize one of Cliff Asness’ pet peeves:

    You may hear some people say they want to buy an individual bond rather than a bond fund. They worry that bond fund prices move around and have no real expiration, so when interest rates rise your losses are somehow more real. But if you buy a bond and hold it to maturity you can put your head in the sand, and never lose.


    This is nonsense.


    You have lost in a real sense since the money you are being returned is worth less in a world in which rates have risen to compensate for inflation. The bond fund is effectively taking your loss today rather than later. If you sell your bond for a loss, you can reinvest at a higher yield going forward. That’s a similar experience to just being in the bond fund. Holding to maturity does not mean you have less risk. It’s an illusion. A real vs nominal illusion.

  2. Using stale marks to “smooth volatility”

    Having a preference for private assets that are less volatile simply because their marks are stale is like not getting bloodwork because you don’t want to find out your cholesterol and blood sugar are too high.

    The slow-to-mark investments are still volatile. The fundamentals of the private business are correlated with the public market volatility.

    Even if you don’t believe your investment should be marked down, then you should be sad you can’t redeem your private investment at par to rebalance into public stocks after the market drops 20%. Giving up liquidity without a premium because it will behaviorally “save you from yourself” sure feels like you sold the option to rebalance at zero.

    I walk through that argument in How Much Extra Return Should You Demand For Illiquidity? (7 min read)

  3. Market prices are clever. They can balance the wagers of path vs terminal value investors simultaneously!

    In What The Widowmaker Can Teach Us About Trade Prospecting And Fool’s GoldI show how the calendar spread options are priced so that the path of the gas price is highly respected, even if there’s strong consensus about the terminal value of the spread (ie the March-April futures spread which is a pure bet on in winter gas being in short supply).

    The OTM calls are jacked, because if we see H gas trade $10, the straddle will go nuclear.

    Why? Because it has to balance 2 opposing forces.

    1. It’s not clear how high the price can go in a true squeeze or shortage
    2. The MOST likely scenario is the price collapses back to $3 or $4.


    Try to think of a strategy to trade that. Good luck.

    Let me repeat how gnarly this is: The price has an unbounded upside, but it will most likely end up in the $3-$4 range. The vertical spreads all point right back to that price range.

    The market places very little probability density at high prices but this is very jarring to people who see the jacked call premiums.

    That’s not an opportunity. It’s a sucker bet.

    Another common example:

    In options land, many investors like to buy 1×2 ratio spreads because the payoffs look amazing for low-probability events. For example, if a stock is $100 and you can buy the $115 call and sell 2 of the $120 calls for zero premium, you think to yourself:

    a) “If the stock does nothing or goes down I break even”
    b) “If the stock goes to $120, I make $5” (or $1 if the stock goes to $116)

    c) “I don’t start losing money until the stock goes over $125. That’s 25% away! This is risk-free return”

    Nah dog. That’s first-time-at-the-rodeo thinking.

    The reason the 1×2 is so cheap is the call skew on the $120 strike is pumped up because someone has been buying them like crazy. That’s where the bodies are hidden. The question you need to ask yourself is “conditional on the stock going to $120 did it get there fast and sloppy, or slow and grindy.” If it goes there in a fast way, the market-maker community will be short beaucoup gamma and be scrambling to buy the $120 calls back. You sold some teenies and went to Santorini and are now getting a margin call on the beach because the 120s you’re short are blowing the f out.

    The path-aware trader is plotting how to be long the scenario where your vacation abruptly ends.

  4. If path is so important, how can you manage to it?

    a) Avoid excessive leverage

    b) Pre-determine when you will cut losses (beware this can be a big topic with lots of room for disaster)

    c) If you insist on betting on terminal value, do it in fixed premium ways where your max loss is bounded. Now you don’t have to worry about mark-to-market risk.

    In There’s Gold In Them Thar Tails: Part 2I cover the topic of path, how to exploit investors’ lack of appreciation for it, and how Jon Corzine became a symbol for path-blindness.

“Long-Short Portfolios All The Way Down”

You’ve heard the expression, “turtles all the way down”.

Corey says “Long/short portfolios all the way down”.

This is an acknowledgment that every trade you make is relative to something else. If you buy a stock denominated in dollars, you are betting that the stock will outperform dollars. It’s a powerful idea. If you want to short XOM but can’t get a borrow, you can buy all the components of XLE except XOM while shorting XLE. Voila, you are now short XOM.

The pirates offer more great examples:

1. Rebalancing

You start with a 60/40 portfolio and stocks go up so the new portfolio is 65/35. You can think of a regular rebalance to get you back to 60/40.

Or you can re-frame the accounting to an algebraic equivalent:

You own a 65/35 portfolio + a long 5% bonds/short 5% stock overlay

It seems like semantics, but just as different words can refer to very similar things, there remains meaning behind the distinctions. And the subtlety here is useful because it forces you to look at the accounting of subsets of a larger position. Corey argues that this lets you think about how things are contributing to your portfolio at any given time or even over time

Bingo.

This lens is the gateway to better p/l attribution. In the 65/35 example, the intuition is fairly basic. Rebalancing trades profit when the market mean reverts and lose money if the market trends. Gamma-scalping works the same way. It’s just rebalancing for option traders. If you trend, your “daytrading p/l” will be negative if it is dominated by gamma scalps and you’ll regret going into work that day (because you will presumably have been hedging your growing delta, for example, you sold the VWAP but the market closed on its daily high.)

I agree with Corey. Seeing the world as long/short portfolios focuses you on the relative nature of every decision! Every time you are long X, you are short [not X]. If you buy a house and it goes up in value along with every other house in your state, when you sell it, did you really make money if the neighboring cost for shelter has appreciated all around you. Start seeing your decisions as long/short portfolios and it has a funny way of focusing you on what you’re specifically rooting for.

2. Corey poses another thought exercise:

Which do you think has a higher tracking error to a passive 60/40?

a) Replacing the passive equity with small-cap value exposure

b) Layering 60% exposure to the SG CTA Index on top

I promise the discussion thread will make you smarter.

I’ll sprinkle in a related idea that comes from options land.

It’s natural for vol traders, especially dispersion traders, to think about positions as a series of long/short portfolios. That’s because all dispersion is “dirty” dispersion. [If you need a refresher see Dispersion Trading For The Uninitiated].

If you sold SPX index vol and only bought vol on value names, your net position is:

  • short growth volatility
  • long value volatility (you are net long, because if you tried to balance your gross index and single name greeks, you’d necessarily have to overweight the value names. This is extra true if you theta-weight the spread since the value names are lower volatility than the growth names.)

If you had this position on before Softbank started buying the hell out of tech calls in the summer of 2020, you got rocked.

But if you put that same position on right before the Covid vaccine was announced, you killed it as value names surged while growth names barely moved relative to their vols.

Index traders are keenly aware of these “synthetic risks” because at some point you’ve been unknowingly exposed to a risk factor that took a bite out of your p/l. That prompts you to slice and dice your risk to further your understanding of positions. Risk management evolves one bruise at a time. The inevitable body shots and jabs hurt, but also teach. You just have to get your overall controls robust enough to survive the haymaker.

[Speaking of teach…did you know that if a stock is halted, you can compute what price the market is implying it will open at? Just compute the price the SPX cash index would need to be at for the futures to be priced fairly to back out the halted stock’s implied price.]

Corey is spot on. It’s long/short portfolios all the way down. This is native vision for derivatives traders.

In closing, know that I’m not just shouting my friends when I say to watch Pirates. That’s seeing causality backwards. Jason is sponsoring Moontower and I met these guys in the first place because I was attracted to how they think (well that’s half of it…there are plenty of brilliant people out there I have zero interest in hanging out with. These are friends that got through the important funnels after I noticed they were smart.) I always learn when I listen to these guys. They’re entertaining and always have good stories.

Actually, you know what? F those guys. Hoggin all the cool in the room.


Last Call

This was a dense issue. Reading is the worst. I know.

Instead of more links to ignore, I will leave you with an invitation to learn in-person.

Me and 2 old friends who all traded at SIG together are going to host 3 free teaching sessions in NYC the first week of October.

We are ridiculously stoked to meet many of you. That said space is limited so there’s a short application.

You can find the details and application in this thread:

Moontower #160

First, Happy Labor Day!

Sorry about Moontower being a day late. I was traveling much of last week then off-the-grid camping until yesterday. Today’s letter is a follow-up to last week’s Moontower. I wrote last week:

Since leaving my trading career nearly 18 months ago I’ve allowed myself a lot of space to explore. I’ve been wary of narrowing my focus prematurely. However, the last few months have started revealing opportunities that warrant deeper dives. I’ll discuss them when it makes sense to. In the meantime, I felt compelled to write about the meta-framework that has helped me filter opportunities.

I published the post this week.

The post will be especially useful to those who @khemaridh describes as having a “pebble in their shoe”. We are all compartmentalized to some degree. But integration is something that matters more to some than others. The cost/benefit varies by individual. Many are bribed by high salaries to work on things they don’t feel great about (ad tech and some finance stuff come to mind). No judgment from me.

No matter how you start out in your career, it’s inevitable that the cost/benefit changes. You can become more inspired or just get bored. Money may matter less or you find you want more of it.

These changes in attitude coincide with changes in your internal compass. I’m not talking about your morality. I’m talking about the sense of your own potential.

You realize that chasing your own potential naturally integrates you.

If you feel uneasy about how compartmentalized your life feels, I’d bet at least even money that you are not reaching for your own ceiling.

I can anticipate an objection already. Especially on Labor Day. “Bruh, I can’t be chasing my own potential, I gotta knock out this rent.”

You’re 100% right. I’m not suggesting you pull the cord, and chase a fantasy. If in this compartmentalized state (think a starving artist waiting tables or cubicle drone who fancies themselves the next Neal Stephenson), you aren’t taking any part-time steps towards your “passion”, it’s not your passion. It’s just a fantasy. I can tell you from my experience of being a horny 19-year-old once upon a time that there are no prereqs to having a fantasy.

But if you want to make your potential and dreams real you have to take actions. You will need to be intentional. Living deliberately, designing your own omakase life, is hard because society offers many pre-made dishes that satisfy your first need — literal hunger. If anything, menus are convenient.

The problem with menus is their designs are highly suggestive. From ads for Happy Hour to the order of the list, the nudges are everywhere. But no menu ever suggests that you check out the restaurant next door. If you walked into this particular restaurant, the management rightly acts as if this is where you intend to be.

That assumption itself is not as neutral as it appears.

The restaurants you see are the ones that can afford to attract you with shiny logos and prime real estate. Imagine it’s 1994. To go off the beaten path you’d to, what, call your friend on a landline for their epicurean input? I’ll just look for the golden arches thank you very much.

The internet changed all that. From Citysearch (I’m old) to Yelp, we could get fed and happy at the same time. And have a new experience. Choice can be overwhelming or life-affirming. (Your perspective has more to do with the quality of your own taste/filters, but that’s a topic for another day). From remote work to new careers to permissionless access to your own audience, the internet has also changed the menu of work.

Am I being cheeky when I compare what you do with your working life with what you choose to eat? I don’t think by much. Sustenance and delight are not the same. To say someone is surviving versus thriving is a softer way of saying that person is slowly dying. Language is a funny thing that way.

So going back to the objection…”bruh, I gotta knock out this rent”. Yes, you do, but don’t forget that’s just survival. Some people are so trapped that is enough. We grade on curves for good reasons. But for you, a person voluntarily reading this utterly whimsical letter where life and death definitely do not hang in the balance, you cannot make this objection convincingly.

The internet has made ordering off the metaphorical menu easier. Embrace it. You can exchange an existential problem (“what am I doing?”) for a technical problem (“how am I going to sustain what I actually want to do?”). You don’t make that trade because it’s easy.

You do it because it’s worth it.

Anyway, that’s a wordy-enough preamble to the longest post I’ve written. It’s part philosophy, part story, and part reference so feel free to skip around.

Design Your Own Engine (31 min read)

The post is the output of observing myself on a lag.

Practically speaking, I felt the need to write it because as I transition my activities from total free-form to even modest focus, it was useful to think about how to narrow attention and consider at least second-order effects of how you could do that in an integrated (more efficient) way.

I talk about sustainability which is a super-category of monetization. I have little experience there but have some meta-principles and hopefully encouraging and pragmatic thoughts for those who aren’t skilled at being commercial-minded (like myself).

Finally some rah-rah at the end that hopefully manages to not be too cliche. Even if it is, you get to see what cliches seem worth bearing mind from the sea of cliches I could have chosen from.

Random bonuses:

  • You’ll learn the very basics of how a gas-powered engine works. (If this is the extent of your interest then do yourself the biggest favor in the world and check out this benevolence by @BCiechanowski.
  • When you see “:[hypertext]” that’s me experimenting with @ncasenmare new Nutshell technology on my blog.

Money Angle

I’m going to stick with a somewhat irreverent tack for Labor Day with this share.

On Meaningless Careers (7 min read)
by Jack Raines

Jack’s Young Money finance blog is consistently fun to read. A few excerpts from this post:

The abstract:

People love work.

The problem isn’t that the youngest generation hates work; the problem is that many of the jobs offered to the youngest generation aren’t work at all. The spreadsheet-heavy, mid-level-manager-dominated, buzzword-filled roles offered to us are jobs, but they are hardly “work.”

For any gamers out there, one of the oldest tricks in the book is giving your younger sibling an unplugged/disconnected controller, so they feel like they are “playing”, while you are in control the whole time.

Many “jobs” today are simply unplugged controllers. The work would get done, whether or not we take part in the process. We are simply moving numbers, smashing buttons, and staying busy, with no regard for actual productivity.

We never stop to ask “is this job necessary?” Because we are paid increasingly higher and higher salaries for our participation in this ever-growing proliferation of pointless jobs.

Sebastian Junger once said, “Humans don’t mind hardship, in fact they thrive on it; what they mind is not feeling necessary. Modern society has perfected the art of making people not feel necessary.”

The concrete:

Football was overbearing, painful, and straight-up frustrating at times, but from day one on the football team, I felt like my contributions mattered.

Contrast that with my experience working in corporate finance.

The people I worked with and worked for in corporate finance were great. My supervisors were certainly nicer than my coaches (which wasn’t a difficult hurdle to surpass, considering some of my football coaches called me things that cannot be repeated over text). And the work wasn’t hard. It was easy, simple. And anything that I didn’t already know how to do could be learned in a few days.

And the best part? I was paid a living wage for my efforts in this corporate finance job. And yet, I hated it. Actually, hate is much too strong of a word.

The opposite of love isn’t hate, it’s indifference. And I was aggressively indifferent to my work.

If pandemic-induced remote work showed me anything, it showed me how little “work” was necessary to do my job. I legitimately “worked” 5-10 hours per week at times, but I was always pretending to “work”, by either moving my mouse to look active or tinkering with files, models, and decks that didn’t really need tinkering to pass the time.

It was pretty obvious that if I didn’t show up for a day, week, or month, the show would go on. I was playing with an unplugged remote.

I was trading my time for a paycheck, with no regard for the actual work being done.

And I wasn’t alone.

The “prestige lie”:

The paradox of modern work is that the most prestigious jobs often involve the least actual work. If you can grind on tedious tasks longer than anyone else, you can get paid a lot of money. You gain material riches at the loss of your individualistic drive.

To quote David Graeber’s Bullshit Jobs:

Shit jobs tend to be blue collar and pay by the hour, whereas bullshit jobs tend to be white collar and salaried. Those who work shit jobs tend to be the object of indignities; they not only work hard but also are held in low esteem for that very reason. But at least they know they’re doing something useful.

Those who work bullshit jobs are often surrounded by honor and prestige; they are respected as professionals, well paid, and treated as high achievers – as the sort of people who can be justly proud of what they do.

Yet secretly they are aware that they have achieved nothing; they feel they have done nothing to earn the consumer toys with which they fill their lives; they feel it’s all based on a lie – as, indeed, it is.

Of course, this whole thing makes sense. Prestige is the lie we tell ourselves to justify our “bullshit jobs.”

We don’t like the work, and in the back of our heads, it feels like we are selling our souls and our time for a paycheck. If we dwelled on that realization too long, we would probably hop off this treadmill entirely. But prestige is that North Star that continues to pull us forward.

The thing about prestige is that it isn’t real. It’s a vanity metric. Don’t believe me? Then why are half of all middle-management jobs now called “vice president?”

Prestige.

Prestige has mollified our collective work restlessness, our existential angst. Prestige keeps those uncomfortable self-realizations imprisoned in the backs of our minds.

Prestige allows the show to go on.

But if you adjust your values, and if prestige loses its luster, the nothingness of these jobs becomes impossible to ignore.

This all ties back cleanly to my post. The prestige “North Star” is one of many compass headings that can leave you with that “pebble in the shoe” feeling.

I’d imagine Labor Day would be an important day for Graeber. A day to celebrate those shit jobs that pay by the hour. They have no prestige but they are honest.

All of this reminds me of this section from 15 Ideas From Morgan Housel’s Interview with Tim Ferriss:

The optimal amount of bullshit

You had Stephen Pressfield on your show, and he was talking about a time when he lived in a mental institution. He was not a patient himself, but he lived there and he starts talking to all these people. And he made this comment that a lot of the common denominators of these people who lived in a mental institution was they were not crazy, they just could not handle or put up with the bullshit of life. They just couldn’t deal with it. And that was kind of why they ended up in the mental institution. And he said all these people were the smartest, most creative people who he had ever met, but they couldn’t put up, they had no tolerance for the bullshit of the real world. And that to me, just brought this idea that there’s actually an optimal amount of bullshit to deal with in life. If your tolerance for bullshit is zero, you’re not going to make it at all in life…

I listened to that [interview] and it was like, “Oh, see, these people could not function in the real world because they had no tolerance for bullshit.” The second step from that is, there is an optimal amount of bullshit to put up within life. And that was where this article, “The Optimal Amount of Hassle,” came from.

And I remembered I was on a flight many years ago and there was this guy in a pinstripe suit who let everyone know that he was a CEO of some company, and the flight was like two hours delayed, and he completely lost his mind. He was dropping F bombs to the gate agents and just completely making an ass of himself because the flight was delayed. And I remember thinking like, “How could you make it this far in life and have no tolerance for petty annoyance, like a delayed flight?”

And I just think like there’s a big skill in life in terms of just being able to deal with some level of bullshit, and a lot of people don’t have that. There’s another great quote that I love from FDR, who of course was paralyzed and in a wheelchair. And he said, “When you’re in a wheelchair and you want milk but they bring you orange juice instead, you learn to say, ‘That’s all right.’ and just drink it.” And I think that just having the ability to put up with that kind of stuff is, I think, really important and often lost in this age where we want perfection. We want everything to be perfect, and it never is.

[Kris comment: I have a good friend who is insanely smart and well-traveled (top 1% in both categories of everyone I know). His brother is not conventionally successful but I was curious what that brother is like. His brother is also very well-traveled in part to choosing a life in the armed forces. But my friend also described his brother as extremely smart. But…incapable of tolerating the b.s. The military life is simple in the ways he prefers. It has always stayed with me, that my friend quite explicitly described his brother as being unwilling to suffer bullshit. I often feel that “getting ahead” in a conventional sense is really just alpining sedimentary layers of compressed bullshit. When I use the word “integrated” metaphysically, a large portion of that is finding your personal sweet spot on the b.s. continuum.]

Jobs like trading and finance are especially vulnerable to bullshit because we put abstractions like price discovery, efficiency, and liquidity on pedestals. Rightfully so. In Finance Guilt, I defend these ideals. The progress of civilization does depend on them.
The problem is that whenever something is good it’s easy to rationalize its excesses beyond the point of diminishing returns. It’s hard to know when more isn’t better.

You have heard the lament that too many wicked smaht people go into finance when they should go into science. What about the genius trading quants who literally used to build weapons for Russia? I’ll leave this for the utilitarians to sort out. Meanwhile, someone who just learned to spell libertarian is hyperventilating “the market will decide”. As if the market’s outputs themselves weren’t downstream of rules set by politicians horse-trading in “the room where it happens.”

Byrne Hobart’s quote brings object-level framing to an abstract argument:

The defense of 1031 exchanges is that they encourage growth because they keep people spending money on new property developments instead of cashing out and enjoying their gains. Which embeds two assumptions:

  1. It’s generally better to tax consumption than investment, and
  2. Real estate investment is a particularly worthy kind of investment to avoid taxing.

Assumption #1 sounds true, but is circumstantial. Assumption #2, though, is hard to defend. Real estate speculation does produce jobs, but it also produces macroeconomic volatility and sometimes threatens the financial system. From a macroprudential perspective, where the goal is to reduce the odds of financial crises, it might make more sense to have 1031 exchanges for everything but real estate: sell your company, and you can roll the money into starting a new one; sell a mall or skyscraper, and you get taxed. But it’s always fiendishly hard to predict the long-term incentives created by a change in the tax code. Any tax on realizing gains, for example, is implicitly a subsidy on borrowing against appreciated assets instead of realizing those gains. If that’s true, the net effect of eliminating 1031 exchanges would be that real estate portfolios would turn over less often. If we assume that people vary in their ability to make good real estate investments, this would mean that the best such investors wouldn’t make as many discrete investing decisions, which would make prices a bit less efficient. Which might be a reasonable tradeoff: making real estate investing a less tax-optimal choice could be a fair trade in exchange for making real estate prices less reflective of their value. But it’s still a tradeoff, not a straightforward benefit. Quirks in the tax code become load-bearing over time; even if they didn’t make economic sense when they were made, the structure of the economy only makes sense in light of the tax incentives that economic actors have already responded to. If you assume that people are reasonably good at reacting to incentives—or, more plausibly, that over time the people who are good at doing this end up controlling more assets—then any change in those incentives has complicated and unpredictable results.]


Last Call

Let’s do follow-up riddles based on last week’s post. You don’t need to read last week to participate. The solutions are at the end of today’s post.

  1. In a follow-up to Another Kind Of Mean:

    You are going on a 2-mile trip. If you drive 30 mph for 1 mile, how fast do you need to drive the second mile to average 60 mph for the entire trip?

  2. A father and son get into a terrible car accident. The father is immediately killed. The boy is taken to the hospital. The surgeon looks at the boy and says “I cannot operate on him. He’s my son”.

    Explain.


From My Actual Life

I went camping for the first time with my family. We’ll do it again.

Solutions to the riddle:

  1. There is no speed you can travel the second mile to average 60 mph for the whole trip. In order to average 60 mph for a 2-mile trip you must travel a mile per minute. So you cannot take more than 2 minutes for a 2-mile trip. If you drive the first mile at 30 mph, you have already driven for 2 minutes.
  2. The surgeon is the boy’s mother. I fell for this riddle when I was in HS. I was reminded of it by a reader in the comments to last week’s post a Sexist Gives A Math Lesson. Here’s the thing…I’ve asked this riddle to many people, male and female. And almost everyone gets it wrong. Their mind goes to harder explanations — it’s a ghost, it’s a stepdad, etc. I’m not kidding, test this out at your barbecues today.

    You know which cohort of people gets it right? Elementary school kids. Even the boys. Do what you want with this.

Moontower #159

Since leaving my trading career nearly 18 months ago I’ve allowed myself a lot of space to explore. I’ve been wary of narrowing my focus prematurely. However, the last few months have started revealing opportunities that warrant deeper dives. I’ll discuss them when it makes sense to. In the meantime, I felt compelled to write about the meta-framework that has helped me filter opportunities.

It’s a long post (it might need to be split into 2 posts for your sake) that is also personal. But I used the personal stuff as a way to move from the concrete to the abstract 2. I saw how to generalize my thinking so you can map it to your own needs. It took a long time for me to see the framework because recent experiences revealed it, instead of me just conjuring it (which I hope means it’s more durable). For those that are in the mental place to receive the post (slight condolences for being in that place — there’s a good chance you’re agitated), I hope it helps.

But, there’s one problem. The dog ate my homework.

The post is only 85% done and still unedited. I’m traveling, then camping most of the next week so inshallah I get it to you by next weekend.

Instead, I give you this.

How The Need For Coherence Drives Us Mad (5 min read)
Moontower

There’s no point in describing this post. Be careful.


Money Angle

Let’s use this section to learn a math concept.

We begin with a question:

You drive to the store and back. The store is 50 miles away. You drive 50 mph to the store and 100 mph coming back. What’s your average speed in MPH for the trip?

[Space to think about the problem]

*

*

*

[If you think the answer is 75 there are 2 problems worth pointing out. One of them is you have the wrong answer.]

*

*

*

[The other is that 75 is the obvious gut response, but since I’m asking this question, you should know that’s not the answer. If it’s not the answer that should clue you in to think harder about the question.]

*

*

*

[You’re trying harder, right?]

*

*

*

[Ok, let’s get on with this]

The answer is 66.67 MPH

If you drive 50 MPH to a store 50 miles away, then it took 60 minutes to go one way.

If you drive 100 MPH on the way back you will return home in half the time or 30 minutes.

You drove 100 miles in 1.5 hours or 66.67 MPH

Congratulations, you are on the way to learning about another type of average or mean.

You likely already know about 2 of the other so-called Pythagorean means.

  • Arithmetic mean

    Simple average. Used when trying to find a measure of central tendency in a set of values that are added together.

  • Geometric mean

    The geometric mean or geometric average is a measure of central tendency for a set of values that are multiplied together. One of the most common examples is compounding. Returns and growth rates are just fractions multiplied together. So if you have 10% growth then 25% growth you compute:

    1 x 1.10 x 1.25 = 1.375

    If you computed the arithmetic mean of the growth rates you’d get 17.5% (the average of 10% and 25%).

    The geometric mean however answers the question “what is the average growth rate I would need to multiply each period by to arrive at the final return of 1.375?”

    In this case, there are 2 periods.

    To solve we do the inverse of the multiplication by taking the root of the number of periods or 1.375^1/2 – 1 = 17.26%

    We can check that 17.26% is in fact the CAGR or compound average growth rate:

    1 x 1.1726 * 1.1726 = 1.375

    Have a cigar.

The question about speed at the beginning of the post actually calls for using a 3rd type of mean:

The harmonic mean

The harmonic mean is computed by taking the average of the reciprocals of the values, then taking the reciprocal of that number to return to the original units.

That’s wordy. Better to demonstrate the 2 steps:

  1. “Take the average of the reciprocals”

    Instead of averaging MPH, let’s average hours per mile then convert back to MPH at the end:

    50 MPH = “it takes 1/50 of an hour to go a mile” = 1/50 HPM
    100 MPH = “it takes 1/100 of an hour to go a mile” = 1/100 HPM

    The average of 1/50 HPM and 1/100 HPM = 1.5/100 HPM

  2. “Take the reciprocal of that number to return to the original units”

    Flip 1.5/100 HPM to 100/1.5 MPH. Voila, 66.67 MPH

Ok, right now you are thinking “Wtf, why is there a mean that deals with reciprocals in the first place?”

If you think about it, all means are computed with numbers that are fractions. You just assume the denominator of the numbers you are averaging is 1. That is fine when each number’s contribution to the final weight is equal, but that’s not the case with an MPH problem. You are spending 2x as much time as the lower speed as the higher speed! This pulls the average speed over the whole trip towards the lower speed. So you get a true average speed of 66.67, not the 75 that your gut gave you.

I want to pause here because you are probably a bit annoyed about this discovery. Don’t be. You have already won half the battle by realizing there is this other type of mean with the weird name “harmonic”.

The other half of the battle is knowing when to apply it. This is trickier. It relies on whether you care about the numerator or denominator of any number. And since every number has a numerator or denominator it feels like you might always want to ask if you should be using the harmonic mean.

I’ll give you a hint that will cover most practical cases. If you are presented with a whole number that is a multiple, but the thing you actually care about is a yield or rate then you should use the harmonic mean. That means you convert to the yield or rate first, find the arithmetic average which is muscle memory for you already, and then convert back to the original units.

Examples:

  • When you compute the average speed for an entire trip you actually want to average hours per mile (a rate) rather than the rate expressed as a multiple (mph) before converting back to mph. Again, this is because your periods of time at each speed are not equal.
  • You can’t average P/E ratios when trying to get the average P/E for an entire portfolio. Why? Because the contribution of high P/E stocks to the average of the entire portfolio P/E is lower than for lower P/E stocks. If you average P/Es, you will systematically overestimate the portfolio’s total P/E! You need to do the math in earnings yield space (ie E/P). @econompic wrote a great post about this and it’s why I went down the harmonic mean rabbit hole in the first place:

    The Case for the Harmonic Mean P/E Calculation (3 min read)

  • Consider this example of when MPG is misleading and you actually want to think of GPM. From Percents Are Tricky:

    Which saves more fuel?

    1. Swapping a 25 mpg car for one that gets 60 mpg
    2. Swapping a 10 mpg car for one that gets 20 mpg


    [Jeopardy music…]


    You know it’s a trap, so the answer must be #2. Here’s why:


    If you travel 1,000 miles:


    1. A 25mpg car uses 40 gallons. The 60 mpg vehicle uses 16.7 gallons.
    2. A 10 mpg car uses 100 gallons. The 20 mpg vehicle uses 50 gallons


    Even though you improved the MPG efficiency of car #1 by more than 100%, we save much more fuel by replacing less efficient cars. Go for the low-hanging fruit. The illusion suggests we should switch ratings from MPG to GPM or to avoid decimals Gallons Per 1,000 Miles.

  • The Tom Brady “deflategate” controversy also created statistical illusions based on what rate they used. You want to spot anomalies by looking at fumbles per play not plays per fumble.

    Why Those Statistics About The Patriots’ Fumbles Are Mostly Junk (14 min read)

The most important takeaway is that whenever you are trying to average a rate, yield, or multiple consider

a) taking the average of the numbers you are presented with

AND

b) doing the same computation with their reciprocals then flipping it back to the original units. That’s all it takes to compute both the arithmetic mean and the harmonic mean.

If you draw the same conclusions about the variable you care about, you’re in the clear.

Just knowing about harmonic means will put you on guard against making poor inferences from data.


For a more comprehensive but still accessible discussion of harmonic means see:

On Average, You’re Using the Wrong Average: Geometric & Harmonic Means in Data Analysis: When the Mean Doesn’t Mean What You Think it Means (20 min read)
by @dnlmc

This post is so good, that I’m not sure if I should have just linked to it and not bothered writing my own. You tell me if I was additive.


Last Call

A few years ago Harvard conducted those “implicit bias” tests and used the results as evidence that even allegedly unbiased people show evidence of unconscious prejudice. I’m not climbing into that cement mixer. But I’ll share 2 quick stories of me catching myself being biased on gender.

  1. Last year, I spoke to a local coding school that said they would hold an in-person class for my son if I could get 5 kids to join the class so it would make sense for them to staff a teacher. I email blasted some parents I knew to ask if their sons would be interested.

    After sending the email, I was kinda shaken that I was looking for “sons”. I told Yinh about it and how bad I felt. In her opinion, I wasn’t biased, she just looked at the list of parents I sent it to and thought it made sense but also since we have 2 boys our parents’ group is skewed (the running joke is if we meet girl parents we really like, it’s like “nice hanging out see you in 18 years”). Yinh didn’t think my actions were evidence of bias but I was suspicious of myself and the verdict is irrelevant. That feeling that I acted in a way that does not accord with my beliefs will help me be better next time. Mistake + growth = all we can ask for.

    Fine.

  2. There’s a project I’m working on in a half-assed way (what else is new?). I was thinking about what it might need if I got more serious. Part of that exercise prompted me to think of who I’d want to be on the board if it became a thing. I wrote a list of names.

    Then I realized it was all men.

    Was this off-the-top-of-my-head list the best list? I opened my CRM.

    [Aside: I keep a database in Notion of everyone I meet, including where they live, what they are working on, what type of help they may need, ie investors or collaborators etc. I recommend doing this. Just makes you a better connector. I have also been keeping a list of every restaurant I have ever to for the past 10 years by location. That way if anyone asks me for a rec, I can look at my phone instead of suddenly going blank. I’m pretty sure I was born to be a librarian or serial killer.]

    When I scanned the CRM, I found multiple women who would hands-down be better choices than the men on the list. Not only that, one of them actually played a part in the brainstorming of the project. WTF Kris.

    I suck. I don’t wanna suck, and I still suck.

    So is implicit bias a thing? It is for me. So I put a checkbox field in my CRM table:

    ”Female?”

    Sounds heavy-handed right? Well, you are free to tell me how I can help myself otherwise, but this is the only way I’ve ever known how to change. Make the thing I want to improve more explicit. What gets measured gets managed.

The subtlety of bias makes it hard to address. What cultural nudges have I silently absorbed that undermine the lessons from the strongest bonds in my direct experience? Consider these following personal facts that have always been top of mind for me :

  • I grew up with a single mother for much of my childhood.
  • I have 1 sibling. A sister who is a brilliant, kind high-achiever.
  • My closest older-than-me relatives are all blood aunts. I have profound respect for their beautiful hearts and can-do-immigrant-tenacity. I have uncles too of course, but only a small percentage of them relative to the women hold my love or respect. (I’m not saying this because I want anyone to generalize about the nature of men vs women, but just to describe how my observations of women have been unusually favorable — on the conscious level).
  • And then I’m married to a woman who inspires me. My wife is an absolute boss but more importantly, has a trail of people who have been touched by her generosity. But she’d never accept recognition for any of it no matter how much they’d want to shout her. However driven she is in professional or measurable ways, her highest priority is her family and friends.

In other words, for the entirety of my existence, I’ve been surrounded by lionesses.

And still, I fail to give women equal consideration without an extra effort. So either the stories we, both men and a special hell-circle of women, tell about why females getting a lesser deal is justified are ego-protecting rationalizations…or I’m alone in being a sexist?

You all have women in your lives that you love. You all have women in your lives you have tremendous respect for or might consider role-models. But that acknowledgment is not a free pass to think you are untouched by bias. Try to catch yourself. Spend some attention on it. And then ask yourself, do you really think unequal outcomes are fully explained by the smart-sounding justifications?

Did fewer girls get interested in coding because I forgot to add them to the carpool? Did the ones who get to hacker camp get discouraged because they were surrounded by farty boys like mine when they arrived? Did the moms not bring their daughters to camp because that idea was less familiar to them since any of the bias that exists today is a fraction of what they faced growing up?

I do believe that over time our awareness of these ideas enlightens us. It just happens over generations. But we shouldn’t take it for granted because it’s not natural to suppress bias. A strained society does not have the energy to suppress bias or prioritize equality. Fear peddlers are opportunists who see people’s pain and sell them scapegoats not solutions. Because solutions to the complexities that weaken a society are hard to see. Our differences are not. They are the first culprits when our insecurities turn to fear.

The word “woke” is stretched to its excess by our mind’s habit of substituting the extremes for the typical. If you label both basic civil rights activism and a fringe effort to have furries considered a protected class as “woke” the word is going to break under tension. So when we push for progress (is that word broken too?), remember there are always people who will pretend there’s none that needs to be made (or that we’ve made so much progress that we need to go backwards).

Maybe I’d listen if they stepped up and told me how bias shows up in their own behavior. If they say it doesn’t, I’ll feel bad for being the only one. But I’ll also know those people aren’t credible.

I get that negative screens work both ways. I’ll let you know how many people unsub. I’ve said my piece. These writers made that easier to do. The cost we incur is still nothing compared to the cost the discouraged bear:

  • The Uphill Battle Women Still Face in High Finance (12 min read)
    by Benn Eifert
  • Markets, discrimination, and “lowering the bar” (12 min read)
    by Dan Luu

    I’ve already wrecked myself today so I’ll comment on this one. Dan uses the term “teenage libertarian”. What a fitting word for the hospital-grade dose of Randian ideology that characterizes so much of Wall Street. I would have described myself as a libertarian at one point but posts like this demonstrate that “market efficiency” is a dangerous expression when used without reference to what conditions must be present for its existence and the degree to which such conditions are unfilled. Libertarianism is as idealized as communism. In their god-given instantiations, both sound beautiful. In reality, one leads to totalitarianism and remains mostly irrelevant as a majority ideal in the US, while the other is insidious because it hasn’t been refuted as the self-serving ideology of those who have been served more than their share (especially if you believe in equality-equity tradeoffs as I do).

    This thread by Benn explains further.

[For the option traders in the room, did anyone else notice the Easter egg in that Dan Luu post? There’s a roll call of thank you’s at the end and one of the people is a Barone-Adesi!]

Stay groovy!

Moontower #158

Patrick posted an ad from a bygone era.

I picture Tim Allen reading that tweet, “They don’t make men like they used to, arh arh!!”

There are a lot of psychohistory comments in that thread but I’m gonna stay on the surface.

Josh commented predictably. He’s a VC and is generally quite vocal about the importance of startup teams working in-person.

[I’m not wading into the binary in-person vs remote debate. One of my smartest buddies runs a SaaS startup with 50-75 employees and would die on the in-person hill as far as the ability to compete in his space. I have other friends running fully distributed trading firms. Personally, I felt like being remote was fine, but I’m old, with established relationships and never worked in places with high colleague churn anyway. I’d just defer to whatever people who run stuff decide is best for their own organizations. I don’t need to have a global opinion on this.]

Ok, I’ll preface this by saying I like and follow Josh. But while his tweet advances his own consistent beliefs, I had the same reaction to the tweet as @ferventfinance — the issue of remote work is impertinent to the ad’s call to adventure.

We are taking Josh’s tweet too seriously, but it got a lot of love and I’m a bit wary of the sentiment behind that. If I had to project, I’m guessing the average person who hearted that tweet would strongly agree with the statement “entitled millennials/zoomers are destroying America”. Ironically, I don’t think Josh would agree with that. And I don’t agree with that statement either.

The sentiment is a close cousin of “people don’t want to work no more”. I’m sorry but if you feel like nodding along with that, hurry along —there are kids who need to be told to get off your lawn. In Nobody Wants To Work Anymore, Joachim Klement humorously (it takes 15 seconds to scan that post) reminds us that serious men have been shaking their fists at clouds for over a century.

And even if the sense that nobody wants to work was somehow more valid today than it was in those old newspaper clippings, you’d have to wonder what prompts that perception. The “back-in-my-day-I-walked-uphill-in-the-snow-both-ways” conservative slant will gravitate to explanations of declining work ethic. The liberal, Zach de la Rocha slant will scream that even if that was true, it was because a regressive system has reinforced Matthew effects until discouragement finally surrendered to alienation.

First, I’ll ask you. If you have any thoughts or want to share links that you found compelling on this please pass them along. I confess. My own impulse leans more towards the RATM side. I said “lean”. The first rule of Fight Club is you never go full Epsilon Theory. [A revealing barometer for this readership is how many people got that reference. I’m always testing you even if you don’t know it. Muahuhaha].

It’s hard to put my finger on it, but it feels like some social contract has been unraveled. That unraveling feels like it’s been happening since the internet took off and accelerated since the pandemic. I’m not a great student of history and any opinion I have about culture at large is discardable as lazy vibes. Instead, I’ll just point you to people who seem to be doing a decent job of investigating the scene of the unraveling.

Last week, I mentioned Rob Henderson’s Happiness Lottery. One of the quotes I excerpted is directly relevant to Patrick’s tweet:

I will never tire of highlighting this simple and profound finding: Sociometric status (respect and admiration from peers) is more important for well-being than socioeconomic status. In his powerful book Status Anxiety, Alain de Botton writes: “Provided that it is not accompanied by humiliation, discomfort can be endured for long periods without complaint. For proof of this, we have only to look to the example of the many soldiers and explorers who have, over the centuries, willingly tolerated privations far exceeding those suffered by the poorest members of their societies, so long as they were sustained throughout their hardships by an awareness of esteem in which they were held by others.”

Look at us today. We worship riches. We have spineless leadership, an assertion that needs no supporting evidence. The richest man in the world is a pathological liar who can’t resist the juvenile urge to move asset prices around with his thumbs. With the energy of a child who takes their ball and goes home, he bluffed that he would actually buy Twitter. He believes he’s above the law and who knows, maybe he is. But he’s long since discarded the looser pro-social ties of honesty and therefore honor.

Start to google “veterans” and this is the auto-complete:

That’s hardly scientific, but don’t you have the sense that the people who serve must look around at the leadership and think they’ve been played for suckers? The idea of doing the right thing feels like it’s becoming…quaint. You’re a patsy in a world of climbers all trying to “build generational wealth” so their children can be above the calls for cooperation3

from which true honor derives.

The children. Oh no, they won’t be failsons. From the grave, our trusts will guide our precious legacies, oops, I mean heirs and grandheirs. We’ll leave them links to threadbois explaining how they too can roll up dentist offices to flip to Blackhenge or whatever fund has $2 quadrillion of AUM and a negative cost of capital. Welcome to the mind of mobile capital in 2022.

Here’s a quaint thought. Role models matter. If people don’t want to go to an office, it’s exactly because there’s no adventure there. It’s not in their bedroom either, but at least they don’t need to suffer the indignity of risking their life on BART so their boss can exit at a high enough multiple to take some time off, before he searches for the CIO that will lead his family office. If the team energized you and you believed you needed to be in-person, you’d go. Note I said “energized” not “incentivized” because we take that word way too narrowly. That was Henderson’s point.

There are athletes who will run through a wall for their team and their coach. That feeling hasn’t disappeared. The people who inspire it have.


Umm, sorry. That got a bit out of hand. I might have blacked out for a second.

Seriously, back to people that are making reasonable guesses about what the hell is going on. Jim O’Shaughnessy (Patrick from the first tweet’s father) hosts the Infinite Loops podcast. He is well-read and gets smart guests who can go toe-to-toe with him in exploring what he refers to as the “Great Reshuffle”. A recent episode with Matthew Clifford made me listen twice. I pulled some takeaways that tie in well with today’s ramblings. You can check them out but I of course encourage you to give it a listen. Matthew is humble, brilliant, clear-eyed yet optimistic (I know that sounds impossible but just listen).

5 Ideas By Matthew Clifford on the Infinite Loops Podcast (14 min read)

If I excerpt here, it will be too long…it was a dense discussion and I did my best to distill what stood out to me. I reduced it to 5 topics:

  1. Modernity as the rise of variance-dampening institutions
  2. The internet as a variance amplifier and the role of ambition
  3. A verdict on whether the internet is a net good or net danger?
  4. Balancing equality and efficiency in the name of self-preservation
  5. Moral luck (which reminded me of epistemic humility as kindness)

For the people interested in Matthew’s prolific knowledge on backing start-ups, the back half of the episode is loaded with insight and a crazy stat about Iranian entrepreneurs in Singapore.

If you want to dive deeper, Matthew’s book was just released Thursday and is already #1 in its category on Amazon. Looks like a great read if you got dat thymos feelin.

How to Be a Founder: How Entrepreneurs can Identify, Fund and Launch their Best Ideas (Amazon Smile link)

[Note this is the Kindle version. The hardcover comes out in October]


Money Angle

First I want to ask a favor. My buddy Dan is interested in understanding how traders and investors would like to consume social data. Here’s a blurb and request by him. Many, if not most of you, (I realize I need to make a survey to learn more about y’all) are market nerds so please give it a thought. Dan is super nice and thoughtful and I think anyone who reaches out will be pleasantly surprised how much they learn while offering their own thoughts. This isn’t an advertisement, there’s nothing for sale.

Social media is the glue that connects our society. Social has disrupted tech, media, politics, and even upended governments. And last year it disrupted our financial system when retail investors took on Melvin Capital over GameStop. Social continues to grow in importance – every day, there are millions of conversations happening around financial assets.

But social is not only a driver of market activity (like with Gamestop), but also a signal. It’s the first place people share news and talk about earnings. It’s where people discuss options flow, commodity developments, and the hottest cryptocurrencies. Social insight mitigates risk, facilitates more complete research, and can be used to find new trade opportunities.

But social data is hard – it’s unstructured and requires significant overhead to properly analyze.  And it’s important to not only account for what’s being said, but who’s saying it. 

Popstox commoditizes and improves on capabilities previously available at only the largest funds and offers solutions for both retail and enterprise. The team brings 10+ years of experience building social analytics solutions for executives at large companies like Nike, Microsoft, Ford, and Procter & Gamble – we know how to make social insights actionable.

We’d love to talk to any traders who are interested in better understanding public discourse around financial assets, either in an individual or institutional context. You can reach out to us at dan@popstox.com – just mention Moontower in your subject line!


Benn Eifert frustrates me. I spend a lot of time trying to wordsmith finance concepts in a way that is sticky and simplified without losing nuance. Benn hops on podcasts and masterclasses this exact task without breaking a sweat. I took notes on his latest Odd Lots appearance. If I can’t beat him at communicating, maybe the next best thing is just having my own work justify why you should care about what sections of the interview I found most important. On a long enough timeline, I’m just a “if you like Moontower, you’ll probably like this” recommendation engine. Someone tell Netflix to buy me out. A 10x multiple on zero is still…doh. Tell’em I’m pure extrinsic and vol is going up.

On to the takeaways:

  • Excerpts From Benn Eifert on the Odd Lots Podcast (14 min read)
    • The craziest aspect of the investing mania of the last few years was the role of sophisticated institutions
    • The role of narratives and how the ability to spin them about the future can become a gray area or market failure
    • There’s a related bit at the end of the podcast that ties back to free market roots of crypto which is ironically self-skewered by grift. (Btw, Wall St is kind of run by people who read Ayn Rand in HS. Whether they unseated the steroid version of it from their minds depends on how convenient it is for them)
    • The challenge of separating hype from real change. The trick is to realize it’s much easier to rule-out than rule-in. What are the flags?
    • Despite the “money printer goes brrr” meme, low rates are not just a “dial that determines the level of speculation”. Although the narrative effect of the meme itself may have been a contributor.
    • Why the froth probably isn’t over
    • Will there be people who learn from the scars and embrace investing more deeply as opposed to just turning their back on what they think is a rigged game?

Last Call

As you guys know I like to share stuff I’m doing with the kids in case you find it useful for your own teaching desires. Lately, I’ve been trying to help Zak (turned 9 last month) learn a bit of Excel. Excel is inherently useful but it’s also a bit of a coding language so it’s a soft onramp to thinking logically and computationally. We did several small Excel projects together this summer. I will IV-drip them to you over time but for today I’ll share one we did just this week.

Zak likes math in general and I often ask him to work on his workbooks (we just got both Zak and his 6-year-old bro Kanagaroo Math books. They require more creativity than Kumon-type stuff and also you can enter their international math competition in March.) Anyway, I asked Zak to “go do some workbook” and he asked if instead, I could give him a bunch of multiplication problems involving 3-digits.

Teaching moment.

Zak, how about we use Excel to generate the questions? He doesn’t know how to do that so we:

  1. Break the problem into small steps.
  2. Use the Socratic method.

If you want to replicate this with your kids, here’s a loose script.

Step 1: We need to generate 3 random numbers.

This didn’t go quite as planned. Zak went to Google and discovered on his own that he could use Excel’s RANDBETWEEN() function to generate a number between 100 and 999. I gave him a ton of praise for being resourceful. This is basic adulting really. But also, I wanted this to be more involved so I said let’s try to do it another way.

Here’s what I asked him:

What digits can exist in each of the ones, tens, and hundreds place?

The very act of asking him put him on alert. He recognized that while the ones and tens place can be 0 thru 9, the hundreds place could only be 1 thru 9. Nice work Zak.

Excel’s RAND() function generates a number between 0 and 1.

How do we make a number between 0 and 9 if we start with an Excel random number?

He realized that we need to multiply the number by 10 but I had to prompt him for a bit.

How do we get rid of the decimal?

Zak: we can round

How’s that going to work?

Zak: we want to round down (after he considered what would happen in both the round up and round down cases. You don’t want 9.4 or 9.8 to ever round up because 10 is not a valid output for our purpose).

Great. Now we get a PEDMAS lesson. Excel solves parenthesis first. With some handholding we arrive at the function for the ones and tens place:

=ROUNDDOWN(10 * RAND(), 0)

The zero was also a good lesson. Excel is not a mindreader, you need to tell it how many decimal places to go to.

But what about the hundreds place? How are you going to convert a random number between 0 and 1 into 1 thru 9?

Zak: [crickets]

Ok, what if you needed to take a random number and convert it to a 1 or 2?

Zak suggests doing what amounts to an IF-Then-Else statement.

Good. What’s another way to do that using multiply or divide?

He got stuck here and I had to play the scenario game with him.

What if we multiply by something other than 10?

And…he lost stamina. That’s ok. We can come back to it. I ultimately explained it, but I’ll ask him to reproduce it soon enough. He still won’t know how and we’ll have to go through all of this again. That’s also expected and ok. Every time we work through it, I suspect the web of thinking fibers thickens a bit, his stamina inches ahead, and most importantly he gets used to the idea that work without a satisfying end is ok. Enjoy the smaller milestone victories along the way. He’s still much further than he was when he woke up because he got to stretch a bit and exercise that little bicycle up there in a systematic way.

Just to be complete about this post, the answer is that instead of multiplying by 10, you multiply by 9 (you are trying to take a continuous range of numbers and bin it into 9 discrete numbers), but remember you must also round up this time, because we want the range to be 1 through 9 not 0 through 8.

Final answer:

=ROUNDUP(9 * RAND(), 0)

From there, just

a) concatenate the 3 digits

or

b) multiply each digit by its respective place (so the first number by 1, the second number by 10, and the one we generated with ROUNDUP by 100) and sum them all together.

We did both methods just to be complete.

And voila, now he can generate his own worksheet of 3-digit multiplication that’s different every time.


I will be sharing some more kid stuff in the future. A select few from the archive:

  • A Socratic Money Lesson For 2nd Graders (3 min read)
  • Hands-On Resources to Teach Kids About Business (2 min read)
  • Bohnanza Is A Great Trading & Business Game (3 min read)
  • Thoughts About Monopoly As A Teaching Tool (2 min read)

From My Actual Life

I just want to acknowledge that this week and last week’s main Moontower essays were kinda snippy. It actually betrays how I’m feeling lately which is extra cheerful. My birthday was 5 weeks ago and since then I’ve given up drinking, processed carbs, grains, caffeine (I cheat about once a week on that but I’ve also been mostly off caffeine since January), and very spicy food. I’m not even drinking bubble water or diet soda. The only liquid I have today is flat water. I’ve also been exercising 5 or 6 days a week even if it’s just attending a foam-rolling type class.

I’m 44. I have high blood sugar, high blood pressure, acid reflux. My family history isn’t great. There’s no imminent problem, but I’m not elastic anymore. It’s harder to lose weight even when I try. It will only get harder as I age, so it’s wise to rediscover higher self-expectations today (yesterday really, but you know that saying about the best time to plant a tree).

I’ve always been unbending about my cold-turkey interventions. It’s not rooted in logic. It’s just what works for me. The interventions self-reinforce each other. When I eat clean I want to exercise and when I exercise I want to eat clean. Irrational or not, I don’t care. I know the desired outcomes and rather wasting time with precision (ahem, analysis paralysis), I’d rather carpet-bomb myself.

Those who know me well, know I’m both a hypochondriac and have a history of self-hacking interventions. I was hardcore paleo for almost 8 years I won a clean eating contest in Crossfit at age 31 and just kept going. Incidentally, I started the contest the day after attending the Kentucky Derby so it was a great way to recover from all the mint juleps and Pappy Van Winkle that ICAP pumped into us. And a mystery I’ll never solve — eating paleo4 somehow cured my lactose intolerance.

Fun fact: Yinh and I even hosted a 9-week paleo challenge for our friends and family. We literally spent 4 hours a night scoring more than 50 people’s food choices (you had to take photos of every meal). The prize pool was about $2,000 and your odds of placing were proportional to your final score. I’m proud to say that there were 2 more challenges led by “graduates” of the first one. We stepped down from administering them because it was way too much work but I’m glad we kickstarted it. Most importantly, everyone learned about what they put in their bodies.

Just a shout-out: I’d bet most of the contestants were the first subs who agreed to receive an email called “Moontower” many years later. Those who have put up with my whimsical ways for decades…hi, I love you all 🙂

There were other interventions too. I did Atkins in college after gaining a Freshman 30. I can remember eating 1/2 stick of butter as a meal once, determined to get the right color on those keto-stix. It’s also what got me into diet soda which was a crappy parting gift. I did intermittent fasting for 3 years from 39-42 years old. Yinh thinks my bizarre experiments struggles have to do with going on Weight Watchers in middle school because I was a fat kid from ages 6 to 13. I’m not sure if WW mattered because puberty was a major reset for me as I lengthened out. Still, weighing my food and knowing calorie counts is muscle memory. I’m not sure if this obsessiveness is a net positive but it’s easy for me to just decide I’m going to cut X or Y. (I’ll admit, cutting booze is hard socially, but since my peers are now older I don’t have to deal with immature peer pressure. Everyone that’s older gets it. In fact, I have felt more respect than judgment from others which is flipped from how this would have went in my 20s. It’s still hard. I like beers and cocktails. We’ll see what happens on all that. For now, I’m fine tee-totaling).

I have never set a time limit on my interventions. I just start. Actually, that’s not true, I once watched a totally unconvincing documentary called What The Health. I was cursing at the screen because I thought it was such cherry-picked garbage that Yinh almost fell off the couch when I announced I was “going vegan” for the next month after watching it. The movie was stupid but I thought the experiment would be fun. (Side note: we want to French Laundry that month for our SIL’s birthday and I stuck to my guns opting for the vegetarian menu. That was a waste of $$).

Anyway, I don’t know how long this will go on but my energy is up, my workout capacity is increasing, albeit from a low level, and my I’m more bushy-tailed than usual. Maybe those cranky takes were just the last of some residue I needed to shake, but upcoming Moontowers will be more focused on usefulness, growth, learning, and all that other quaint stuff done in my California sober (I recently heard this expression) way.

Moontower #157

I didn’t get a chance to write the essay I wanted to this week. I allude to why in the From My Actual Life section.

Instead, you get links with grouchy commentary.


The Happiness Lottery (9 min read)
by @robkhenderson

Excerpts:

  • It struck me that I don’t feel “relaxed” unless I’m working. Many people would explain these tendencies by referring to the inherited trait conscientiousness or something. But that’s far from the sole factor…I attribute my shift in habits to two different factors. One is a change in my social circle. I still have friends from my old life. But I have left many habits of that old life behind. My new social circle is largely comprised of strivers. People who work relentlessly. And, for better or worse, I have adapted to this. But there’s a related factor. There’s this impending sense that I have to make up for lost time.
  • In 1963, 20 percent of Americans lived in poverty. Today it’s 2.3 percent. In low-income neighborhoods, the problem is not primarily economic. In low-income neighborhoods, the problem is not primarily economic. I will never tire of highlighting this simple and profound finding: Sociometric status (respect and admiration from peers) is more important for well-being than socioeconomic status. In his powerful book Status Anxiety, Alain de Botton writes: “Provided that it is not accompanied by humiliation, discomfort can be endured for long periods without complaint. For proof of this, we have only to look to the example of the many soldiers and explorers who have, over the centuries, willingly tolerated privations far exceeding those suffered by the poorest members of their societies, so long as they were sustained throughout their hardships by an awareness of esteem in which they were held by others.”
  • There’s been a renewed discussion about the role luck plays in life outcomes. Much of this has been sparked by a new book titled The Genetic Lottery. A key idea is that none of us chose our particular endowments. IQ, personality, and other variables that predict life outcomes. Thus, the author of the book and many others argue that we should favor redistributive policies to help those who got the short end of the stick. I’m not opposed to financial assistance. But the focus on economic redistribution overlooks something. There is more to life satisfaction than money. The renowned behavioral economist Daniel Kahneman has written: “Income is an important determinant of people’s satisfaction with their lives, but it is far less important than most people think. If everyone had the same income, the differences among people in life satisfaction would be reduced by less than 5%.” Giving people a bunch of money isn’t suddenly going to improve their lives. But since highly-educated people primarily understand value in terms of dollars, it’s worth noting the following: -In terms of the effect on happiness, having a friend you see regularly is worth $100,000 a year -Being married is also worth $100,000 -Seeing your neighbor regularly is worth $60,000 -Other research suggests that income doesn’t have a lasting increase on happiness because people usually adapt to money. In contrast, marriage, family, and health have lasting increases on happiness and are immune to hedonic adaptation. Compared with not attending any religious service, attending a religious service once a week has the same effect on happiness as moving from the bottom to the top quartile of the income distribution A poor person with a spouse, a close friend, a relationship with a neighbor, and who attends a religious service can achieve the same level of happiness as an affluent upper-middle-class person. Today, poverty is lower than it’s ever been in the U.S. And yet happiness is falling. The idea that material circumstances are the primary determinant of our subjective emotional states and the organization of our social lives is a weirdo Marxian theory. But it somehow became the conventional wisdom among educated people.
  • As I pointed out in the above findings, our relationships are at least as important to life satisfaction as money. Yet our elites are reluctant to promote marriage, friendship, social bonds, neighborliness, etc. The non-material factors that give rise to a rich and fulfilling life. Somehow we’ve become reluctant to publicly endorse any sort of value that lies outside of economics. Governments are paying people to take vaccines. Cities are paying residents not to shoot people. Leaders have become reluctant to appeal to higher ideals or principles. The belief seems to be that all that matters is economic incentives. In a 2019 New York Times op-ed, two Nobel laureates share research findings indicating that people overestimate the strength of economic incentives. The authors report that “status, dignity, social connections” are more powerful drivers of behavior. So why the focus on economic redistribution? Many reasons, some noble.

    [Kris comment: I have an essay in my drafts that argues for a specific version of redistribution and I’m waiting for a mood when I’m ready to lose a bunch of subs to publish it]

    But one is that promoting friendship and marriage doesn’t hurt one’s enemies. Malicious envy is the strongest predictor of support for coercive redistribution. Rich people want to hurt people richer than themselves. If the richest 90-99th percentile of people discovered that marriage among the poor would inflict pain on the richest 1 percent, then that 9 percent would be matrimony’s strongest supporters.

  • My favorite bit because it explains why I grew up on 3rd base even if not financially: You and I might know something about what it means to live a satisfying life. But we didn’t “earn” whatever traits we have that led us to this understanding (and the associated happiness). So, the logic goes, we should share our knowledge with those less fortunate than ourselves. We can give money to people to help them out. But we can also promote wise choices and strong norms to help them out. The fortunate among us can share our wealth, sure. But we might also share our values—steps we have taken to live fulfilling lives.


Money Angle

I have 2 links for you to check out this week.

Economic Misconceptions Of The Crypto World (8 min read)
by Noah Smith

Crypto is simultaneously fascinating and frustrating. The frustrating part of watching “number go up”, has been watching:

a) legalized grift and pumping. This can range from sewer-dwelling spammers to podcast-darling VCs who spout new-age word salad and clever analogies from the same set of sci-fi books.

b) newly flush financial tourists speaking like experts on matters of investing and economics. A charitable classification of this group is honest but not yet competent. Their confidence is just “beer muscle” (I realize this would hit harder if I wrote it 9 months ago, but just look at a 3-year chart of BTC and it holds as long as you don’t know the difference between time-weighted and dollar-weighted returns).

The “a” group knows who they are. They can jump off a bridge. Incompetence is one thing, but being smart and dangerous gets you negative respect and a forever loss of trust in my book. (There is a path to redemption: you can always donate your dirty gains to charity and unwind the Bay Area home price increases you spurred with the fiat you exchanged for bags of coal. If your eventual attempt at penance is nothing more than a “ReformedVC” Substack where you litany all the “story-telling” and “narrative-building” persuasion tactics you employed it isn’t gonna make the @ladder_is_kicked_crypto_is_my_only_hope Twitter anon feel any better.)

The “b” group, if they care about learning, should read Noah’s post. It explains 2 important economic concepts:

  • Cash is not savings
  • Scarcity doesn’t necessarily create value

Noah is an economist so I’ll let his post explain those ideas but I’ll add a bit that seems intuitive to me for no other reason than I’ve played Monopoly. The fact that the money supply grows whenever you pass GO is a clue. This is totally unacademic so feel free to correct me:

Money’s primary purpose is liquidity — to reduce transactional frictions. The money supply needs to increase with the population.

Imagine an island economy with coconuts, hut-building labor, and surf instructors…they could use seashells as a medium of exchange to solve the double coincidence of wants problem. If the seashell supply were fixed, then as the economy grows the seashells would be deflationary (meaning everything of value in the economy would go down in value relative to the seashells). And crucially, liquidity would dry up. Money would not fulfill its promise of facilitating trade because islanders would horde seashells.

When the population grows there is more supply and demand for goods and services. Population growth means economic growth. GDP increases. (Note that for GDP per capita to grow, which is what we ultimately desire to raise standards of living, productivity needs to grow. For example the ability to grow more coconuts with the same labor. We call that agriculture.)

BTC ultimately has a fixed supply. It’s like the seashells. If the technology known as “money” is useful because it creates frictionless transactions, aka liquidity, then a fixed supply is a counterproductive design.

[I’ve heard people argue against this by saying BTC is divisible into tiny amounts.

<Headscratch emoji>

Brb, lifting a 4-slice pizza so I can cut it into 8s and sell it to you for a profit.]

To be complete, BTC’s scarcity can make it a store of value even if it’s not great as a form of money. Cash is a store of value, but only temporarily, and that’s ok because, well, read Noah’s article.

(One last parenthetical from me…gold and silver are somewhat divisible and scarce. They maintain some collective acceptance as money. They have also been stores of value. But they have satisfied these roles as “stores of value” and “money” in uneven ways. I can’t buy bread with silver at the store. Its volatility in dollar terms is much higher than the annual standard deviation of CPI and as long as I need to convert silver to USD to buy stuff, this volatility spread matters. As a store of value, gold and silver real returns have beaten inflation on the centuries time scale, but since your life is lived in decades there’s a lot of tracking error. Unless you’re a cat, the experience of your life happens once so you need to decide how problematic that tracking error is.)


New Substack recommendation: The Old Rope by @varianceswap

Here’s a fun excerpt from the latest issue:

Real estate in the private market exists in between the two preceding applicable stock market concepts: you want to buy quality, and you want to buy it at the price you’d buy distressed assets at. But you’re okay just buying quality- after all the private market real estate investor needs to find an asset to 1031 exchange within 45 days of a sale. Readily available dirt-cheap bankruptcy-remote leverage from commercial lending operations provides the private real estate investor with a nearly-government-guaranteed reasonable return. Buy quality and stay rich (never pay taxes).

Because private market commercial real estate is private, rarely do these quality assets sell at generous prices to counterparties outside of the “boys’ club” or in-network, off-market participants for whom favors have already been traded, country club memberships have been synched, and alumni events have been planned. This is what I would call the System 1A of real estate investing. This is where common misconceptions occur with real estate: generalist laymen see these slam-dunk transactions and the seemingly risk-free returns generated from them. They observe “dumb people” getting rich not knowing these people are actually repeat-players in a multi-generational game. They play nice with each other to stay in the club and stay rich.

Damn, this brought me back to some of the cronyism in the trading pits. On the NYMEX/COMEX floor brokers were also allowed to be traders. They could trade for their own accounts, but they were not allowed to trade against their own flow. Well, if you can imagine the incentive, you can imagine the outcome.

Here’s the scene: market makers stand in a pit while brokers run their business out of surrounding booths. The booths were the phone banks outside the pit where broker clerks would talk to the “upstairs” customer. If a juicy market order, especially one without a lot of risk or deltas such as a tight vertical spread or butterfly, there was a silent feeding frenzy. Sal couldn’t trade against his own flow, but knew that Tony would get him “next time”. You know, like a running bar tab. Better yet, maybe your sister starts her own brokerage competing (cough) for the same flow.

If a 100 lot of butterflies traded in the pit for a credit (you heard that right…the meat of a butterfly trading over the wings) you can safely deduce that several hundred lots never made it to the pit.

It’s worth reprinting the last line of that excerpt:

They observe “dumb people” getting rich not knowing these people are actually repeat-players in a multi-generational game. They play nice with each other to stay in the club and stay rich.

And if resentment to this old word order wasn’t high enough, we had the experience of watching some of these “dumb” people who owned several, sometimes tens of seats on the exchange, receive nearly $10mm a pop for them when the exchange demutualized.

[Side note: I worked for a SIG at the time who owned a bunch of seats. They made a bonanza buying NYSE seats before the stock exchange went public so they were ready for the same trade ahead of the NYMEX IPO. One of our assistant traders spent most of his time going to the admin office in the building to find the bid/ask on seats and get the color on who was looking to buy or sell. Probably didn’t take much more than regular coffee and donuts to keep in the office clerk’s good graces. On a personal note, I got some shares as part of the seat lease agreements that SIG had to (probably begrudgingly, since prop firms are ruthless maximizers) give to the people whose names were actually on the lease. The IPO priced at $59 bucks but the NMX shares opened on the first day at $120. I sold the opening print along with many other traders. It was a free $25,000 or so. The stock closed at $152 that first day so I left a lot on the table, but even worse was that my mind’s comparison monster left me feeling sour. A lot of folks down there became generationally rich.

And if they were smart, took the money and ran. It was a countdown to the end of floor trading.

[Extra salt in the wound — there was some arrangement where you had to sell your free shares through Merrill (I think) and they charged like a $500 brokerage fee. And yes, this was 2006, not 1966.]

Enough story time. Go read The Old Rope. The second post I’d read is:

Fake Life, True Wealth (2 min read)


Last Call

Productivity Hacks

  • Here’s a neat Excel feature I happened upon:

  • I have been color grouping my browser tabs in Chrome for at least 6 months. Just right-click on any open tab and choose “Add Tab To Group”.

    (If you find it bogs your machine down see the tweet replies for related tools)


From My Actual Life

I incinerated, or should I say Shitibank, incinerated a day of my life this week. I closed the checking account I’ve had for 22 years.

I switched to First Republic. Here’s the story…

Stay groovy!