the art of paranoia

This is a fun one.

A good friend and mentor from the pit sent me this (lightly edited and hyperlinked):

I was catching up on moontowers and reading your cotton story. Made me think of one that you can use if you ever cover interest rates.

I started in trading with silver options. I was quite meek as I had never clerked. I was just backed and thrown in the pit at age 22. Anyway, a couple of years in, silver had rallied from around $4 to $7. The whole pit was short long dated $4.50 calls to a spec who was holding the long. These things were easily exercisable as interest rates were high. Great short to have.

Broker [badge redacted] (you may remember him) offered the synthetic put at zero. No one knew what he was doing. I bid 2 ticks under and he said sold.

So I said “1000”. I think the biggest trade in that pit was like 200.

Anyway I took 1000, exercised them and made 10 grand before commissions. The carry was probably north of 50 ticks and he increased his shorts by around 800 as all the other locals got hit with my exercises. The other locals were pissed.

So I came in through a broker and bid 2 ticks under the next day. Locals hit me. I got lucky because I was clearing [redacted prime broker] and they neglected to put in my exercise. They delayed it by mistake (and gave me the interest as I recall.)

Anyway the locals thought they found someone who would hold these things and just wanted a synthetic put for a credit. I kept doing the trade for a week.

[Redacted broker] got it right by the second day. I think I made another 5 or 10 grand before the locals figured it out and stopped doing it.

Anyway. I hope if you relay this no former silver option traders subscribe. They still don’t know it was me!

 

There’s a lot going on here!

Option pricing mechanics, pit dynamics, deduction.

Let’s start with the option pricing.

I don’t want to deny you the opportunity to figure that part out for yourself.

In the following list, I’ll start with important clarifications but as the list unfolds the material is more of a hint than just reference information.

Like a quiz show, buzz when you understand why “locals” [ie the other traders] were willing to” sell 2 cents under” and why my friend was willing to buy that level.

Clarification and hints…

  • 1 silver option references 1 silver future. This is typical in commodities whereas equity traders are used to an option having a multiplier of 100
  • 1 silver future references 5,000 troy ounces of silver. So if silver is $10 an oz, it’s a $50,000 contract
  • The minimum increment, or “tick”, in silver options is .001 or 1/10th of penny. Since it references a 5,000 oz contract, a penny is worth $50 and a tick is worth $5.
  • This story happened many years ago. Look at those silver prices: “Silver had rallied from around $4 to $7. The whole pit was short long dated $4.50 calls to a spec who was holding the long.”
  • Silver options are American-style meaning you can exercise them anytime.
  • “Random assignment”: when an option is exercised, any contract in that series held short is equally likely to be assigned regardless of the clearing firm or account. See rules.
  • When a broker quotes a “synthetic put” (and yes synthetics are not just identities but directly traded orders!) the convention is to bid or offer as a “differential to intrinsic value”. When my friend bid “2 ticks under”, it’s understood that he’s willing to pay 2 ticks under “intrinsic value”. If the futures are $7 and the broker sells the $4.50 call 2 ticks under than the trade package is:
    • broker sells the $4.50 call at $2.498 to my friend
    • brokers buys the future for $7.00 from my friend
    • Make sure you understand this: to buy a synthetic put it to buy call and sell the future “1-to-1” (meaning for every option you buy, you sell 1 future.) Another way to express that is you hedge on a 100 delta. A synthetic put is assumed by everyone to be a simultaneous package of “long call, short future” in the same way as a straddle is call + put on the same strike or strangle is call + put on different strikes. “Synthetic put” is a real tradeable thing not just the name for an option identity.
  • While futures are subject to initial and maintenance margin, option premiums are settled in full. In other words, the premium is not itself marginable. That is normal but worth stating because there are some option markets where the premium is marginable (ie WTI options on ICE)

At this point, you should be able to understand my friend’s side of the trade. If you don’t want to bother, stick around, I’ll spell it out soon enough but also that part should feel really obvious to anyone that’s ever owned an American option.

The harder question is:

Why were the broker and the other locals willing to sell him the synthetic put 2 ticks under?

Your last hint is a line already tucked into the story:

The whole pit was short long dated $4.50 calls to a spec who was holding the long. These things were easily exercisable as interest rates were high. Great short to have.

This is fun stuff. Let’s unpack it.

Why did my friend buy the synthetic put 2 ticks under?

It’s an American-style option. He buys the $4.50 call for $2.498 and sells the future at $7.00.

He exercises the call immediately, effectively paying $6.998 closing out the future he sold at $7.00. He makes 2 ticks or $10 actual dollars x 1,000 contracts. $10k profit (before exchange fees which probably claimed ~ 25% of that). Call it $7,500 for a minute’s work and no risk.

How could my friend’s buy be so good if he also says:

The whole pit was short long dated $4.50 calls to a spec who was holding the long. These things were easily exercisable as interest rates were high. Great short to have.

The key:

The carry was probably north of 50 ticks

50 ticks = 5 cents

In other words, the interest on $2.50 of intrinsic option premium was 5 cents or about 2%

💡While a market-maker will be hedged with futures, you only need to post margin to maintain that leg. You can satisfy the collateral requirement with T-Bills, so you really are capturing the the interest on the short option premium without having it offset by hedge funding which is close to zero.

💡In the story, there’s 5 cents of carry. If we knew the DTE, we could back out the interest rate prevailing back then. If we knew the interest rate, we could back out the DTE. But we have neither. We just have the recollection that the call had about 50 ticks of carry.

Think of the typical local’s position:

The whole pit was short long dated $4.50 calls to a spec who was holding the long.

The locals are hedged. They are short the deep in-the-money calls and long futures against them on a 100 delta. In other words, they are short synthetic puts. The puts on that strike are worthless however if the spec never exercises the calls, the locals will get about 50 ticks of interest. It’s like selling a worthless put for a nickel.

💡If you’re so Taleb-pilled you can’t imagine a put being worthless, just pretend you could buy the actual $4.50 put for a tick or the $4.75 put for 3 ticks. There’s such a thing as arbitrage bounds. Options 101 stuff.

Amateurs will say things like “that’s worthless” because they believe a price “can’t get there” but when I say it’s worthless I mean by arbitrage. Like the value of the put on that strike is dominated in such a way that if you could sell it at a positive value there’s free money on the board. An option trader thinks in a matrix of arbitrage relationships when they examine a chain.

You can see why the locals were willing to sell the put 2 ticks under. They didn’t think they would get assigned! They assumed they were going to collect 50 ticks on a riskless position.

The mistake was in thinking my friend wouldn’t exercise the calls. Perhaps they thought he needed to cover risk and if they were all short the calls he was just closing. But that doesn’t make sense to me since he was a “meek” trader before then and certainly wouldn’t have been short 1000 calls.

That’s the most puzzling part to me. I understand why they might believe a customer like the spec would not exercise the call optimally, but when a market-maker buys them you need to update. “This guy who trades options all day is buying an American-style option below intrinsic, I wonder what he’s going to do?”

I don’t want to be too snarky because “street smart” is probably one of the most salient features of a pit trader. I’ll assume I’m missing a detail that makes their decision justifiable.

 

The rude awakening

“The other locals got hit with my exercises. The other locals were pissed.”

This is the random assignment. When my friend exercised his calls the free interest gravy train slowed down as suddenly some of the locals got assigned which closed their positions (the short call goes away and the long future they were hedged with is liquidated to the exerciser).

💡In random assignment, you “expect” to be assigned on your pro-rata portion of the OI held by all shorts. How many you actually get assigned on can vary from this theoretical expectation because the sequential 1 by 1 assignment process is memoryless just like dealing from a deck of cards with replacement each time. Just because you got tagged on the last one doesn’t change your odds of getting tagged on the next one.

Let’s keep unpacking the story.

Poisoning the well

My friend masked his behavior to blend in with customers and used a broker to “bid 2 ticks under” the next day. The locals didn’t think it was a market-maker going through a broker. The locals were reasonable in not suspecting a local to be hiding themselves behind a broker order for 2 reasons:

  1. Paying commission which would eat into the slim margin even further.
  2. This behavior is known as “poisoning the well”. This type of pro vs pro crime was considered bad form. Just like in poker how the pros try to avoid each other and just eat the fish. Of course from the outside, the norm is considered anti-competitive.

Let’s address both of these.

Regarding #1:

My friend may have worked out a deal with the broker. After all, the broker stands to make a thousand bucks or so for no real effort and if the order is contingent on a reduced commission rate they’ll probably go for it.

[I used to do this all the time. Wet the brokers’ beak. We like to talk about nerd stuff and math here, but trading is a business like any other business. Giving out orders is currency. Traders who pay lots of commission magically get the first call. Whether it’s commodities or equities brokers can solicit the other side rather than bring an order to the pit and instead just cross it without worrying about the order being broken up (ie bettered) they can double-bill. Brokers are fiduciaries and their business is competitive, get too many bad fills and you risk losing a customer, but there’s a lot of leeway in discretion. I’m using a broad brush, the rules and details vary across asset classes, but the mechanics rhyme everywhere.]

Regarding #2:

Prisoner’s dilemma.

How much is it worth to defect?

Will we return to stasis and you got away with one or did you really poison the well?

Will anyone find out?

Does any of this change if you don’t really fit in with the club and can’t hope to be part of it?

And then there’s pure disagreeability mixed with self-confidence. I was at Max’s soccer game last weekend and the ref in a moment of deprecating humor said “They told me when I was a kid you need to either be smart or likeable. And I’m definitely not smart”. I don’t think this particular buddy ever cared about going along to get along. But he’s also super-smart.

I’ll add my own perspective to the game theory stuff. I did nothing but watch markets get tighter, more competitive and more ruthless over time. The edge you never would have settled for becomes something you’d kick grandma down the stairs for before you know it. Someone is going to defect.*

This is chained to another observation. In a landscape where there’s excess profit (ie too much reward per unit if risk) there is always someone sandbaggin’. They aren’t showing how smart or fast they are because they will harvest at this level before it tightens and not have to tip off to others what’s possible. I know this firsthand because of a friend that runs a brilliant trading operation in a niche space in which he never shows the market how fast he really is. Imagine my lack of surprise when I read about this “don’t show” tactic from HFT-er Liquidity Goblin’s Let’s Pretend We Have An Edge (paywalled).

A fortunate mistake

I got lucky because I was clearing [redacted prime broker] and they neglected to put in my exercise. They delayed it by mistake (and gave me the interest as I recall.)

Anyway the locals thought they found someone who would hold these things and just wanted a synthetic put for a credit. I kept doing the trade for a week.

[Redacted broker] got it right by the second day. I think I made another 5 or 10 grand before the locals figured it out and stopped doing it.

My friend was able to milk the ruse for a bit longer because of an error! The prime broker failed to process the exercise which reassured the locals briefly that they were not getting picked off. Sounds like it gave him at least another day to buy more synthetic puts for a credit before the locals got wise to the game.

Knowing is half the battle

Let’s put a bow on this like an 80s cartoon ending lesson.

Being short those synthetics to a single counterparty who doesn’t realize the calls should be exercised is good fortune. But once someone wants to buy those deep ITM calls opening, you know that they know what they’re doing.

I’ll tell you from personal experience that anytime someone wants to trade a deep option or a reversal/conversion where there is little or no open interest your guard goes up. You check your funding assumptions. You think harder about what your option model is saying about the value of an American vs European style rev/con. The difference between the 2 represents the value of the early exercise option for that strike. Those are modeled via trees simulations and difficult to debug as opposed to closed form equations for European Black-Scholes.

Only the paranoid survive.


 

*I refer you to this excerpt from A Former Market Maker’s Perception of PFOF:

SIG wasn’t know as the “evil empire” on the Amex just because of the black jackets we wore. They understood the risk-reward was completely outsized to what it should be 25 years ago. They were amongst the first to tighten markets to steal market share. They accepted slightly worse risk-reward per trade but for way more absolute dollars. They then used the cash to scale more broadly. This allowed them to “get a look on everything”. Which means you can price and hedge even tighter. Which means you can re-invest at a yet faster rate. Now you are blowing away less coordinated competitors who were quite content to earn their hundreds of percent a year and retire early once the markets got too tight for them to compete.

SIG was playing the long game. The parallels to big tech write themselves. A few firms who bet big on the right markets start printing cash. This kicks off the flywheel:

Provide better product –> increase market share –> harvest proprietary data. Circle back to start.

The lead over your competitors compounds. Competitors die off. They call you a monopoly.

deworsification?

Let’s start here…

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

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

This stood out to me:

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

Umm, the quiz:

Article content

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

I tweeted this a few days ago:

Article content

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

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

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

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

What would you rather own?

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

OR

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

Stuff you can read if this is not clear:

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

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

See the GFC through a quant’s eyes

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

To complete the point:

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

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

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


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

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

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

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

From Why Does Volatility Matter?:

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


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

So-Called “Bonds” in Prediction Markets

Great subtitle:

Rare events teach slowly

why poker is used to train traders

This video is the best articulation of why poker is used to train traders.

From the description:

Jerrod Ankenman, professional poker player, co-author of The Mathematics of Poker, and Quantitative Researcher at Susquehanna, explores the connections between poker and trading. Jerrod, who began his career playing poker and went back to earn his PhD, explains how concepts like probability, expected value, risk management, and game theory apply in both the card room and financial markets. Poker and trading both demand strong mathematical thinking, disciplined decision-making, and the ability to manage uncertainty under pressure. Jerrod shares lessons from his poker career (which includes a WSOP bracelet win) that translate directly into quantitative finance and trading strategy.

If you are a trader this video despite not being technical is alpha. It tells you where to look if you pay attention.

A few ideas I’ll re-emphasize:

SIG treats poker as a structured way to train probabilistic thinking. Jerrod structures the flow of the video as a parallel between 3 concepts in poker and their analogs in trading.

  1. Ante
  2. Decision practice
  3. Interpreting outcomes

You’ve heard this before — both poker and trading require making decisions with incomplete information. But a more subtle point is about speed. The goal in both is the same:

“Make the decision now that’s as close as possible to what you’d decide if you had infinite time and information.”

Both poker and trading have an information structure of what’s private and what’s public. But also what’s behavioral. Examples of the trading version of these ideas:

Private info: proprietary models, internal data, trader knowledge sharing.

Public info: news, filings, Fed releases.

Behavioral info: order flow and price action. In other words, what others are doing.

This last point gets a lot of emphasis and maps strongly to poker because at its core, it recognizes that trading is an adaptive, adversarial game not a physics problem. It’s an evolving pattern recognition and categorization problem.

You can’t model every opponent individually, or every trade uniquely, because you shrink the statistical power of your findings. You must intelligently group similar situations into profiles. Familiar poker examples: “tight-aggressive regulars,” “recreational loose players”. In trading, profiles can account for who (ie retail), periodicity (time of day, time of month, and so forth), or why (index rebalance, hedging mandates).

The art is balancing taxonomy and specificity to have enough data to be statistically meaningful, but close enough to be relevant.

A few other powerful ideas:

The big risk isn’t volatility.

It’s being wrong about your edge. The market wiggles are the nature of the game, that’s not a risk.

[I’ll take a moment to repeat myself — if you blow out because the market moved, you were committing malpractice. Being aware that the market will do things amounts to no more than a toddler understanding of risk. Volatility shouldn’t keep you awake at night. That the exchange might cancel your trades or that they may ban orders should.

From Investopedia on the response to the Hunt Brothers’ silver squeeze:

Federal commodities regulators introduced special rules to prevent any more long position contracts from being written or sold for silver futures. This move stopped the Hunts from increasing their positions by temporarily suspending the fundamental rules of the commodities market. With longs frozen and shorts free to pile in, the price of silver began to slide.

From my floor days, I can tell you there’s lore about who knew the valuable bit of info that you were only going to be allowed to do opening trades on the short side. Exchanges were run by the traders and brokers before they went public. This is the weird black or grey swan stuff that bosses worry about.

A company going bankrupt? That’s a line item in portfolio_shock_analysis.xls, not something that makes you cry in public to your investors.]

Back to Jerrod. A big risk is being wrong about your edge. It’s a risk because edge hides behind low signal-to-noise. This is one of the great teachings of poker. Short-term results are noise. He explains that in Limit Hold’em, even a high edge hand has only .02 big bets worth of expectancy vs a standard deviation of 2.5 bets.

[Kris: In investing language, a .008 Sharpe for one trial. The SP500 has a daily expectancy of about 3 bps and 100 bps standard deviation for a daily Sharpe of .03. The poker hand has almost 4x the noise of the daily SP500 return.]

Since poker teaches that you will make the right decision and still lose money, it trains you to emotionally decouple decision quality from result quality.

This is a ceaselessly profound concept. Not because it’s so clever, but because of how it resists internalization. It’s easy to understand, it’s hard to apply the understanding to how we receive the world. Fooled by randomness might be a tired title, but it’s never been stronger as we are bombarded with data.

The risk of being wrong about your edge is insidious because the relative efficiency of markets means it’s hard to make excess returns, but it’s also hard to lose too much doing sensible things. The problem is when sensible things aren’t adding value beyond randomness, but you think they are. You’re wasting your life tossing coins.

[Unless you like action for the sake of action. In that case, you’re understimulated. Go take a risk in the name of actual growth or something.]

The link between speed and skill

Jerrod notes that you don’t have time to “go to the lab” mid-hand or mid-trade. Edge requires building mental shortcuts and intuitions that perform well under time pressure.

This feels easiest to imagine in the world of sports. I’ve heard elite athletes talk about how the big jump from say college to pros is “just” the speed of the game. It’s not that they are doing new things, it’s that they must be able to do the same things faster without losing precision.

I remember reading a profile many moons ago about Jason Kidd who was known for his passing and court vision. I got the sense that he could see a split second into the future. Being able to make and execute a decision just a tiny bit faster compounds into outlier results over time. The long-term ROI on having your intuition slightly better tuned works to disproportionate effect.

This echoes. We play the mock trading games and some people are just a tad faster every time. Maybe when new info hits the game they refresh their market quickly, not necessarily making a perfect 2-way, but it’s biased in the direction of the asymmetry. Ricki Heicklen discussed this with Patrick McKenzie. If you are trading “the sum of the siblings in the room” and someone’s count is revealed, do you Bayesian update in the right direction and in a proportionally coherent way? When you see someone do this consistently, you know they’re clocking differently than the others (and I’m excluding the clueless whose updates are logically incoherent to how they processed a similar situation in the opposite direction).

In competitive scenarios, if you can debug your thinking in the moment, you’re too slow. When making a market for a broker, you need to hear the order, intention, what’s not said and how the trade looks vs the framing of the option chain in seconds (and this of course assumes your tools are already designed with this workflow in mind, showing you the info you need when you pull up the ticker). This is obviously not happening if you need to step through expected value trees. There’s no substitute for reps if you need to decide faster than the speed of system 2 axon to dendrite sex.

Feedback loops to build that intuition

Jerrod is blunt. The best way to learn in poker and trading is post-mortem discussion. Go over the tape with your team. Chat scenarios. A great feature of trading is if you love it, you want to talk about it, so this doesn’t feel like work.

When I was at Parallax, I used to carpool with 3 other traders. Shout out to Steve, Ben, and Rob — I still wish we livestreamed those rides. The commute in the morning was your typical sports or current events banter (ok fine, gossip). But the ride home was all play-by-play of trading scenarios from the day. What happened, what would you have done there, etc?

While Jerrod treats discussion as the primary way to learn (I agree — trading is an apprentice craft) he does acknowledge a role for books.

[Even though I recommend some books, they are more for describing the overall epistemic landscape or inspiration. 99.9% of what I know about trading comes from discussion or experience. I either learned how to price or think about something from someone else or after discovering first-hand a new way to lose].

He mentions that most poker books are wrong. He offers a strategy for figuring out which ones are good. But he also encourages reading the bad books because it reveals how your opponents might think. That bit reminded me of an old post I wrote:

Twitter Reminds Me Of The Trading Pits

[Random: I was hanging out with a trader from my cohort who now runs education for a big prop firm in Chicago. He was re-learning poker because a lot of the stuff we learned 25 years ago is now considered wrong. I’m not surprised, since 1 year of poker information in the online, poker-on-ESPN, poker-celebrity-giving-TED-talks era likely generated a decade worth of info from 20th-century poker.]

In sum, SIG is using poker to build the same mental circuitry that trading relies on in an enclosed, fast-feedback petri dish. It’s speedrunning experiential learning in a low-signal environment so the requirements of a successful trading career seem less alien. If trading were as easy as “just study and you’ll get good grades”, motivation and time would be sufficient ingredients. With trading and poker, you could have infinite time but if you don’t know how to learn, you’re pushing on a string.


Related to ideas in this post:

  • Trading Is A Team Sportdispelling the lone wolf image and reminding you that forums, Discords, chats make learning together easier than ever
  • 5 Takeaways From Todd Simkin on The AlphaMind Podcastif you like the material above, you’re gonna eat this up
  • Another storied trading firm, Peak 6, is using poker to train. Co-founder Jenny Just admits she was late to the game on this but when you hear what they’re doing you’ll see they are making up for lost time. The poker stuff is at the end of the episode. Most of the conversation is about them buying sports teams.

 

the messiness of options in the real-world

Recently, I’ve been writing a lot about option funding — implied rates, reversal/conversions, and financing stock positions, and even a touch on early exercise. The posts from earliest to most recent:

You can’t really overstate how important this is, especially to pros.

On the same theme, Stanford lecturer and HF manager Kevin Mak published an outstanding and detailed post:

Holding a high cost to borrow stock? Here’s how to collect the borrow fees using the options market (link)

I want to quote a few key parts:

I cannot stress enough that if you want to be competitive in capital markets, you cannot afford to make these types of mistakes and forgo this return.

Kevin is quite blunt:

If you think this is too complicated to follow, to be blunt, you likely do not have the mental fortitude to have alpha in markets (you may still make money via luck). If you CAN figure this out, but couldn’t be bothered to spend time on it, that’s probably fine, but I suggest staying away from holding a stock with a high cost to borrow. If you insist on holding high cost to borrow stocks, and “not worry” about collecting the free borrow/lending fees, you really should be playing triple-zero roulette, or splitting every pair of 10’s at Caesar’s Palace instead because that would have a lower edge, and be way more fun.

I suggest that by using options to refinance your position, you “inherit the market maker’s funding rates” which are almost certainly better than yours, whether you are long or short.

This is Kevin’s way of saying this which might land better for some (emphasis mine):

If this is arbitrage, it shouldn’t exist right? This unique situation is you “arbitraging” your own holdings. You’re basically holding an inefficient asset since you can’t lend it (or collect the lending fees) so this lets you own it in a more efficient manner. Nobody is going to compete away this arbitrage because nobody can access your holdings except you. In fact, it’s the arbitrage happening in the open markets which is pushing the value of synthetic long to be equal to the long stock (and collect borrow) position.

Kevin wisely tucks all the brain damage into the endnotes to not ruin the flow and central message of the post. I love his intro to them:

This is a beginner treatise on a synthetic long position and covers ~98% of what you need to know about it. The last 2% I could write 25,000 words about and not be finished.

In the spirit of the endnotes, I want to share a recent real-world example of a scenario that resides in that annoying “2%”

Alex, a mutual of mine on X, asked the following:

I bought some deep itm $AIV calls, I think Jan exp, a couple weeks ago because I thought they were cheap vs my financing cost. Not much extrinsic value… Underlying had silly spike after hours, up then down.

Was the right way to trade this, to short the underlying after hours? I thought about exercising to sell, but didn’t want to burn a few months of time value for nothing, even if I didn’t really pay for it.

I’m going to step through the conversation, injecting meta-commentary to bring it down a level.

Me: Your trade expression was because of financing but you are asking about what you should have done with your delta. I’m not being pushy, I’m just trying to help you answer your own question.

There are 2 things I can see so far:

  • Alex is conflating his strategic financing decision with tactical delta management. I do the Socrates thing as a habit when learners entangle multiple issues into a single question. If I just jump ahead and answer each part of the implied questions, I rob Alex of a valuable opportunity — to debug his own thinking by breaking the big question into its components. I notice many people getting option or trading concepts rolled into a ball of yarn, which tells me they don’t understand each string as well as they should. When you’re forced to decompose your own question, the deficiency is self-apparent.
  • He’s showing good instincts about not wanting to exercise the calls because he’d be “burning a few months of time value.”

💡Option Pricing Clarifications

  1. The first [but not final] check on whether you should exercise a call is if the value of the OTM option on the strike is worth more or less than the cost of carry.
    1. For an ITM call, is the dividend you are exercising for worth more than the put on the same strike?
    2. For an ITM put, is the interest on the stock short if you exercise greater than the call on the same strike?
  2. Alex said he thought about “exercising to sell,” but to be clear, you can’t exercise the calls after-hours and have it settle the next day. There is a cut-off for exercise notices. He would have needed to short the stock after hours, then exercise the next day, meaning he would have to carry a short for 1 day. This tactic would have flattened his delta, but he would have to incur any financing ramifications for the 1-day short.

This simple scenario highlights a risk to using heavily-discounted synthetic futures to express a long:

If you plan on liquidating the length before expiration, you are exposing yourself to the change in funding that you otherwise locked in.

In this case, Alex is exposed to the borrow he may have to pay on short shares if he chooses that route to cut length. One day’s borrow, even if steep, is unlikely to make or break the whole trade, but the bigger issue is the “locate”. There might not be any shares to borrow from your broker. If Alex was long the stock instead of the synthetic stock, he could just sell it in the after-market.

If Alex chooses to cut length by selling the ITM call, it may be for the same discount that attracted him to buying them in the first place. It’s like buying a home for a discount because it has lots of street noise. It’s a problem you can’t outrun because you will be on the losing end of the discount when you sell the house.*

Stay groovy

☮️

 

*Tangential, but I see people misunderstand this in the private school vs public school debate. If you pay up to live in a good school district, you are exposed to 2 risks:

  1. The carry cost on the premium. If you pay 20% more for a good school district, the funding cost on the extra ~20% of mortgage is the cost. If schools are the deciding factor between an $800k or $1mm house and mortgage rates are 5% then your pre-tax cost of the better schools is ~$10k per year. This is probably much less than private school tuition, especially if you have multiple kids.
  2. The perception of school quality. The “school premium” can expand or contract over time. You can win or lose to this when you sell.

In general, the true cost of the premium you pay for good school districts is very small relative to private school tuition, making your VORP hurdle for private school choice high (although worth it for many people).

VIX futures vs VIX synthetic futures

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

This is from my IBKR screens from 10/22:

Spot VIX was 18.4

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

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

The combo or price of the 22 synthetic =

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

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

No arbitrage available folks (as expected).

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

💡The VIX options and futures typically expire on the Wednesday morning preceding monthly option expiry cycles. The options cannot be traded between the prior night's close and the Wednesday settlment but the futures can.

vol trading is easier than directional trading

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

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

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

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

Which brings me to volatility.

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

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

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

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

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

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

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

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

what hides in the option chain

We’ve been talking about option funding stuff recently in the paid Thursday issues. Recently, I had a trader ask for some help making sense of an option expiry in a single name that trades by appointment but where some chunky size goes through.

It’s a name with lots of hair on it with respect to events and distribution.

[The current mark of a big option trade that went through a few weeks ago is still rattling in my head. I’m looking forward to where the roulette wheel is gonna land on this thing!]

I’m obviously not going to give away the name, but I can recycle some of what I explained to the client using a fake stock.

It’s rooted in funding and why understanding it is frankly critical for making sense of names that have wide markets. You’ll see :

  • the first thing that caught my eye when I looked at the option chain
  • put-call parity’s relationship to a vol curve
  • how to avoid making really dumb trades (or if you’re a broker how to look like a hero to your client)

We can do this with screenshots and commentary to make this tour brisk but rich.

We begin with an invented option chain for our fake stock. I chose these values to be in keeping with the quality of the real stock’s markets without giving anything away.

For any junior traders or trainees this is good diagnostic practice — to eyeball an option chain and take notice of what’s interesting.

Relevant background info:

✅European-style expiry (it’s complicated enough without early exercise)
✅No dividends
✅RFR: 4%
✅DTE: 43
✅Stock price: $108.50

What do you notice:

Don’t start all nerd mastermind. Instead observe. These markets are wide!

Well, before you start thinking “The 125/130/135 call fly is negative, yay free money”, you should recognize that the market widths are obscuring this vol surface. I mean, if you think you can trade at mid-market, there’s free money all over this board. All kinds of bells should be going off but just as a surgeon has a checklist, there is definitely a priority thing to look for.

Think a bit before I offer a hint.

 

Ok, here are 2 columns that should help:

IVM = “IV Mid”

Categorically, the call IVs are greater than the put IVs on the same strike.

 

It’s safe to assume the stock is $108.50 as I indicated in the setup.

So what’s the likely culprit?

The rate.

We used RFR = 4% but with that rate put/call parity is not holding.

This is messy since we are using the mid of wide markets, but I didn’t contrive this situation from scratch— it is based on a real snapshot the client showed me on a screenshare, so it’s an opportunity to address real-world complications.

If call IVs is categorically higher than put IVs then the IV is being computed from a rate that is too low.

Instead of imposing a rate, let’s try something else. We will require that put/call parity hold at each strike.

💡Review the method: implying the cost of carry in options

This table is a handy way to start:

I highlighted the 110-strike because it’s closest to the $108.50 spot price.

The right-most column shows the implied yield of each strike. By computing an implied yield the call and put IVs are forced to be the same but I left the stale ones in the table for the sake of this chart:

It demonstrates that a difference in call and put IVs is another way of saying the implied yield or cost of carry on each strike is different.

If you impose put/call parity, forcing the IVs on the strikes to be the same (I didn’t recompute the IVs on each strike here with the implied rates from their strike), then instead of seeing a chart with call and put IVs not lining up you’ll get some implied rate curve across strikes like you see here.

Let’s look at this like a checklist:

✔️If the call and put IVs differ across the strikes when imposing a cost-of-carry parameter (as we did with 4%) then the market is telling you your cost-of-carry parameter is wrong.

✔️Instead, impose a market-based yield by starting with the no-arbitrage assumption of put/call parity to get call and put IVs to line up.

✔️But if this leads to large disparities in implied rates across strikes, well, we still have a puzzle.

Looking at our rate curve…we still have a puzzle.

Experienced traders know why, but just to bring it along gradually, here’s another table that will look very familiar to anyone with an ETF, index, or options arbitrage background:

Computing the implied market by calculating the implied synthetic stock futures bid and offer.

Remember, the synthetic is just the combo price (c-p) plus the strike price. In the prior table we based our synthetic prices on the midmarket values of the options.

Here we want more detail. For each strike, we calculate:

synthetic bid = call bid – put offer

Take the 110-strike as an example to consider what this means…if you hit the screen bid on the calls AND simultaneously lifted the screen offer on the puts, effectively crossing 2 $3 wide markets (before you got fired), you have sold the synthetic future at $107.

We compute the implied yield bid/ask using the implied combo bid and offer with the same logic. [Again, to turn option combo prices into implied yields see this post.]

The puzzle as to why we are getting a ridiculous range of implied yields is not too mysterious — the markets are just too wide. Garbage.

We will do our best with what we have because there’s still plenty to see.

The art of computing the vol surface

The preferred way to set a vol curve is to imply the rate, then impose that on the surface to generate strike vols. Since the implied rate on each strike based on mid-market won’t be perfectly uniform (although likely much better than this stock) you will still get different call and put IVs on the same strike but they are not likely to “cross”. In other words, you won’t be able to lift a call option on a strike for a lower IV than you can sell on the put (or vice versa). The error in IV should be within the market widths.

To give you a flavor of how you impose an implied rate on the strikes across the same expiry we can consider a few methods.

The tightest market

We cobble together the best bid and offer from any of the strikes to imply a yield. I don’t love this method for actually estimating the rate, but it’s the fastest way to spot an arb! Look at all the implied rates…the 75 strike really sticks out like sore thumb. If you hit the call bid and lift the put offer you have synthetically sold the stock at $109.80. If you buy the shares for $108.50, borrowing to finance them until expiry in 43 days, you will have legged a “conversion” trade for a fat profit.

Trader math — I borrow $108.50 for 2 months at 5% (notice conservative assumptions on both days and rate) that’s 1/6 * 5% or 80bps on $108…call it 90 cents. So I buy stock for $108.50, sell it at $109.80 and pay $.90 in interest…$.40 pure profit. Manage to get filled on 50 combos? That’s $2k in 2 seconds. Annualize that.

I’m getting carried away. This kinda thing is never just sitting there because it’s easy to program a bot to “eye” for it and then if it does find it, it’s because you ingested stale data. Still, I hope I conveyed the benefit of the “tightest market” method even if the benefit accrues to speed demons.

Weightings

How else can we find an implied rate to impose across all strikes? We could average the implied yields we find at each strike but give more weight to strikes with tighter markets (in this case, every market is $3 wide so the strikes would get equal weight and given the widths — still garbage).

We can just choose to look at a range of strikes near-the-money. We can weight their implied rates by inverse distance to the stock price. We can exponentially weight tight markets. We can draw hard cutoffs on strikes that exceed specified widths. You can use a solver across strikes but even then you probably filter the strikes according to criteria that come from experience.

[And when it comes to American options, may god have have mercy on our souls. The value of rev/cons can vary widely across strikes as the probability of early exercise differs. You are very much triangulating across several unknowns because the probability of an option being exercised also depends on its vol so you end up falling back on some ordinal relationships that bound early exercise relativity between strikes. In English, it’s easier to say relative things about early exercise adjustments to rev/cons than it is to absolutely value a rev/con. If there’s one area that even experienced traders trip up on its American options. Through the grapevine, from multiple sources, I’ve heard that one of the largest market makers in the biz lost a meaningful proportion of their annual profits because their mispricing of early exercise was exposed during the rate hikes in 2022.]

Anyway, there are enough choices involved that no 2 firms compute vol surfaces starting with implied rates in exactly the same way. There’s no benefit to bogging down on a specific method for this post so I’m just going to impose the 11.65% rate from the 110-strike and re-compute IVs.

With the single rate, the call and put IVs come closer together especially for the near-the-money options. The deep OTM options are going to stay a problem because a $3 wide market on a .15 delta option is just a lot of vol points of noise. [The vega on those options is much smaller than ATM, so $3 represents more vol width.]

Towards a single vol curve

Usually when you look at a surface, it’s just a single vol curve through all the strikes for a given expiry. A common way to do this is to simply use the IV from the OTM option. That option tends to have a tighter bid/ask width since it has less delta risk for the quote streamer.

If you don’t want to dismiss all the information from the ITM option on the strike, you could weight the IV inversely to the market widths or even to the options’ contribution to the straddle price on the strike. Here’s the vol curves using the OTM method and the Inverse Contribution To Straddle method:

Looks like a “W”.

If you have been paying attention to all the stuff I’ve written about vertical spreads and butterflies, you can guess the implied distribution:

bimodal

And yes, the original stock I helped the client with does indeed look bimodal. This is also a distribution you often see on stock earnings.

[My group used to call it the “teepee” and I heard from some transplants that it was another famous market maker who made a lot of money “teaching” the market that this was the right shape for a vol surface in particular situations.]

While this fake stock is the spawn of a real bimodal stock, this is not the most interesting thing about the surface.

By far the most important thing to see is that the implied rates are totally jacked!!! The calls are leaned incredibly high relative to the puts. You have to be able to see this right away (or infer it from the call IVs being high relative to the put IVs if you use a platform that doesn’t impose put/call parity on ATM mid vols).

Calls should never be too high relative to puts because conversions are easy arbitrages especially in non-dividend-paying stocks.

[In conversion trades, you sell call, buy put, buy stock. You must fund the stock purchase so you are exposed to rising interest rates. But that is the only material risk.

Reversals which entail buying call, shorting puts and shorting stock are exposed to declining rates but also any suprise dividends or the stock becoming harder-to-borrow. That’s why you almost never see implied rates trade much higher than SOFR — it’s easy to arbitrage via conversions. But implied rates often trade far lower than SOFR because borrow is uncertain. If you do a reversal trade because you want to exploit the implied rate, your most likely outcome is to find out the rebate you anticipated on your short stock was wishful thinking].

What can you do if you notice the calls are too high relative to the puts?

The eager beaver is going to say “do a conversion arbitrage”. I appreciate the optimism. But those markets are wide. Those mid prices are fake. You can’t get filled anywhere near mid if you try to sell calls or buy puts.

But that’s the clue.

What do you do with the knowledge that the implied rate is too high if you can’t do conversion arbs?

You simply don’t buy calls or sell puts anywhere near mid-market. You are walking into a trap. If you are a broker or advising someone, you explain this to them as well. You’ll save them a bunch of money and they’ll appreciate that you know your stuff.

[This also helps manage expectations. If you are a broker and given an order to sell calls into this market, you should point out that the implied rates are high, meaning the calls are leaned up, and the customer shouldn’t expect to get filled near mid. Similarly, they wouldn’t be able to buy puts near mid either as those are leaned down.]

 

In closing, when you look at an option surface there are so many invisible decisions about how to compute the IVs. When you see call and put IVs that vary greatly, your instinct should be to imply the rate. This post has been in the recent tradition of “options are ALWAYS about vol EXCEPT when they are about funding” but I hope today’s effort has actually shown that we can’t actually compute the vols without understanding funding.

One of the funny things about options is that while variance is an abstract concept to trade (the square of standard deviation??) it’s a straightforward bet — the outcome of the trade is tied to the intent. The payoff reflects the expression. If the realized volatility will be low, sell this.

Meanwhile, listed options, literally called “vanilla”, these American-style shape shifters tradeable from your phone are a pile of path-dependent, hard-to-solve “halting” problems, being discussed by weekend-house-flipper salespeople because there are so many ways to win or lose that are unmoored to your original intent that the randomness of the experience makes them perfectly marketable despite their basics being inscrutable to their average user.

I hope this post made them a little less inscrutable to you.

so you’re interested in trading…

Friends,

This is a follow-up letter I wrote to someone who called me interested in learning to trade. Look, trading is a neat career for many reasons (I discuss that at the end of my chat with John). But if you don’t enjoy the material below, it’s probably not a job you’ll like or excel in. Finding that out alone is worth diving into this. From the outside, it’s easy to get a mistaken impression of what trading is. It’s also easy to conflate it with investing.

None of the below material is technical. If you consider it technical, you’re a little bit behind but not drastically if you enjoy the material because that means you can catch up quickly. If the thought of learning this basic stuff sounds like a chore, really, just leave now. No judgment.

[Just as a matter of calibration. If you read this letter regularly, you can use me as a benchmark. I’m not technical by the standards of trading in 2025. I was more on the technical side of traders about 15-20 years ago. If graduating today, my education is too general to get hired as an assistant trader at a prop firm. You can still differentiate yourself by demonstrating an exceptional proof of work in the form of projects, entrepreneurship, leadership or competitiveness. But the bar is high.

Technology is leverage. 99.9%-tile is 1 in a 1000 while 99.0% is one in a hundred. In winner-take-all games, you want mutants not common valedictorians. At this point, my experience is what makes me valuable. My aptitude is average for this field, and below average, for many of the directions it’s heading in.

Luckily in America, how much signal you are doesn’t decide your prosperity. There are a lot of rich idiots because randomness is blind. The less skill you have, the more you want to play roulette not chess. Crank the vol. If you look at the trading or asset management worlds, can you capably classify which jobs are roulette and which are chess? Look at the winners in certain investment-related jobs and you can start to figure it out. This is called being strategic about what you should do and comes way before “I want to be a trader”.

A recurring theme: calibration is everything. Knowing where you are in a pecking order and choosing your actions in light of that is a life skill. You don’t need to be especially smart to do that, but you do need to be self-aware. That means interpreting feedback without your defensive ego scrambling the message.]

In short, trading is competitive. You need a genuine interest to maintain the required persistence when the going gets tough, which it always does. This is true of every competitive field.

Anyone promising easy returns is either:

  • inexperienced
  • stupid
  • lying

In other words, running a grift or flattering an ego gassed up by luck.

If I haven’t deterred you, enjoy the letter…


[name redacted],

As promised, here’s a short list of resources I think you’ll really enjoy if you’re interested in markets, decision-making, and risk. These cover a mix of foundational ideas, practitioner insights, and a few of my own essays.

Trading starts with a general way of thinking — what service does the market need that it offers a return for? Think of these resources as the mental operating system on which the tactical labor runs.

Remember, while investing is compensation for patience and risk tolerance, trading is compensation for research and labor. Work. And that work must outmaneuver the work of the competition. It follows that this will lead you to look for easy games where the best competitors are less likely to look (in fact understanding their barriers will be part of your prospecting).

If you google “trading systems” or anything related to making money from the comfort of your home, there is a high likelihood it’s the equivalent of house-flipping seminar lead gen. It’s a space rampant with unserious grift and marketing.

There is no shortcut. This material is groundwork and since it’s not project-based, should be done fairly quickly (I give some roadmap below). One of the primary benefits of working through this material is seeing if these ways of thinking resonate.

If it’s a drag, you’ve learned a lot about what you’re not interested in, and this is valuable, time-saving knowledge!


Books

  • The Most Important Thing — Howard Marks’ lessons on second-level thinking shines because it’s so approachable. The Gladwell of professional investment writing.
  • The Laws of Trading — Agustin Lebron connects adverse selection, psychology, and rational decision-making. If Mark’s book is a 101, this is the 3rd-level thinking grad course without being formal or technical.
  • Thinking in Bets — Poker player Annie Duke emphasizes one of the hardest but most fundamental principles in decision-making – restraint from judging outcomes by whether they worked. She teaches you to separate decision quality from result quality, embracing probabilities, updating beliefs, and thinking in expected value rather than absolutes.
  • Superforecasting — Philip Tetlock’s research on probabilistic thinking and what separates great forecasters. It’s a manual for improving accuracy and something even more important — calibration.
  • Fooled by Randomness — Nassim Taleb’s classic on luck, risk, and the illusion of skill.
  • Adaptive Markets — Prof. Andrew Lo on the evolving predator/prey dynamics in markets.
  • Retail Option Trading — Euan Sinclair and Andrew Mack’s practical look at option trading frameworks. Although focused on options, the messages are delivered in the context of general principles you must internalize. So think of it as “how they apply the OS to options”. You want to focus on the application more so than the option details.
  • Books by Andrew Mack — worth exploring if you want to dive deeper into what research looks like
  • Poor Charlie’s Almanac — Slipped this in just because. Even middle-schoolers should read it.

Podcasts

  • Risk of Ruin — thoughtful, narrative-style interviews with traders and gamblers exploring the psychology of edge and risk.
  • Bet The Process — focused on sports betting but full of probabilistic and behavioral lessons applicable anywhere.
  • Flirting with Models — Corey Hoffstein’s excellent conversations on quant finance, risk management, and portfolio design (more advanced, so this is aspirational. A glimpse of down the line.
  • Founders — stories of entrepreneurs told through deep dives into biographies, rich with insights about iteration and resilience. Generally motivating. Lots of timeless, simple ideas.

Blogs

  • Money Stuff — Matt Levine. Best finance writer on Earth. A daily habit of reading this will rewire your brain.
  • Robot Wealth — practical, data-driven experiments in systematic trading and learning.
  • Kid Dynamite’s Blog — not currently active, but the archives are incredible for plainspoken lessons from a former trader.
  • Michael Mauboussin’s Essays — an incredible collection of writing on expectations, capital allocation, and decision-making.
  • Newfound Research Blog — Corey Hoffstein again, blending quant research with clear, thoughtful writing.

Moontower Essays

A few of my own writings that expand on themes like volatility, edge, and how traders think:

This portal will help get your brain trained to more probabilistic patterns:
Moontower Brain Plug-In

This portal introduces you to a foundational, often underappreciated understanding of investing: Moontower Money


If I had to pick where to start, I’d say:

1. Howard Marks book

2. The RobotWealth Blog

3. Laws of Trading book

4. Thinking in Bets book

5. The select Moontower blog posts including the Moontower Money portal (the Brain Plug In is more of an ongoing thing to refer back to for brain food).

That should take about a month of reading in the evenings after work ( ~ a book + 2 blog posts per week).

Then I’d read Mauboussin…there’s so much there, it’s not about reading all of it but go with what sounds interesting. His way of thinking infuses everything he writes and those are the thinking habits you are trying to absorb.

Start here:

Probabilities and Payoffs The Practicalities and Psychology of Expected Value

Then from this link try:

Untangling Skill and Luck: How to Think About Outcomes – Past, Present, and Future

From this link try:

The Paradox of Skill: Why Greater Skill Leads to More Luck

The Importance of Expectations: The Question that Bears Repeating: What’s Priced in?

From this link try:

Min(d)ing the Opportunity: Excess Returns Require the Chance to Apply Skill

IQ versus RQ: Differentiating Smarts from Decision-Making Skills

Bootcamps

If you’d like to do a course I’d recommend:


I’ll close with something I told John Reeder near the tail end of the Risk of Ruin episode.

John prefaces my comments with:

Despite the fact that Kris writes about how to learn the math of options and about behavioral elements of trading — and despite the fact that a lot of this stuff is offered for free — some people are just not going to get it.

My take:

It’s gonna sound maybe harsh, but I tend to think that if you’re gonna figure it out, you just kind of are. You’re gonna find what to read; you’re gonna find the right things. And it’s like, if you’re unable to do that meta work, you’re just not cut out for it.

This is competitive. If you need to have your hand held just to figure out what’s good content and what’s not — you’re already cooked. Honestly, I really do try to be optimistic, but I think the people who are capable end up finding what they should be looking at.

On average, it probably works out that the people who are going to figure it out will end up finding the people who would have been their guides. I don’t think anybody’s born knowing how to do any of this. I’m very SIG-pilled in that way — I think you can learn. I don’t think everybody can learn it. I’m not saying that. You absolutely need some sort of minimum threshold of certain characteristics.

John to the audience:

Kris told me he sees a problem that exists today — a widespread rejection of experts. And he says that really isn’t going to work if the goal is to learn. Even the very top people that firms like SIG hire — brilliant, brilliant people — still have to be coachable.

So if those people have to be coachable, then everyone else trying to learn the same material, probably without even close to the same aptitude, can’t start the whole thing by rejecting the idea that there’s anything to learn.

I close that section with:

What does SIG do as soon as they hire somebody? They humble the shit out of them. Every single person they hire is smarter than almost everybody you’ve ever met. But what do they have to do? They have to cut them down a bunch of notches and say, “See everybody else in this room? They’re all trying to do the same thing you’re trying to do. And by the way, you’re not any smarter than any of them.”

So unless you can be taken down to where you’re ready to learn — to become a sponge, to become coachable — it’s not going to work.

implying the cost of carry in options

This is the follow-up to last week’s the easiest win in options is for stock traders.

In that post, we started with a puzzle that leads to a critical insight:

The collective pursuit of option arbitrage means that we can use put-call parity in reverse — to imply the cost of carry instead of assuming one, THEN trying to impose put-call parity.

In the example of the $100 stock and 4% SOFR rate, we computed the cost of carry or what we formally call the “reversal/conversion” or R/C was $3.92.

synthetic future = C – P = intrinsic Value + R/C

where:

C = call value on the 100-strike

P = put value on the 100-strike

The fair value of the synthetic future in our example is therefore:

→ synthetic future = intrinsic Value + R/C

→synthetic future = (S – K) + R/C

→ synthetic future = (100-100) + 3.92 = $3.92

I expect the call to be trading for $3.92 MORE than the put on the 100-strike if the stock is $100.

If it’s trading for a larger premium than $3.92 then there should be an arb:

  • Sell call, buy put [short the synthetic future]
  • Buy the stock

This is a “conversion trade and since the cost to finance the long shares is the 4% we used to compute fair value, I should have a profit left over.

If the call is trading at a discount to $3.92 vs the put then I should be able to do a “reversal” arbitrage where I:

  • Buy call, sell put [long the synthetic future]
  • Short the stock

The interest I collect on the proceeds of the short sale should exceed the premium I paid for the synthetic.

That’s the theory.

Of course, if you’re fair value differs from market pricing, guess who’s probably wrong.

Instead of using some assumption about the cost-of-carry, we invert:

“What does the cost-of-carry need to be for put-call parity to hold?”

It’s hard to overstate how powerful this inversion is. It has profitable applications to retail option traders, directional stock traders, both long and short, quants modeling option surfaces, and even fundamental investors concerned with dividends.

Conveniently, the lowest-hanging fruit affects the largest groups — directional stock and option traders. We will cover this in detail while keeping explanations shorter for the more professional applications.

We start with a question:

Have you ever noticed that the call IV and put IV for the same strike on an option chain are NOT equal?

This is all going to make sense soon. With some basic mechanics and simple algebra we are going to discover a whole new order book for stocks.

Solving for r: volatility is not the only thing we imply

We are going to take this journey in small steps.

We start with our identities to build our “if-then” muscles:

where:

K = strike
r = risk-free rate
t = fraction of a year

If r increases, R/C increases as the gap between the strike and strike discounted to PV widens.

Let’s re-arrange the synthetic future identity which includes the R/C to be in terms of the call and put respectively:

→ Synthetic future = Intrinsic + R/C

→ C - P = (S-K) + R/C

If r increases, R/C increases, therefore, calls go up in value while puts go down in value.

The heuristic:

When interest rates are higher the opportunity cost of buying shares increases or the cost of leverage increases if you buy on margin. Arbitrage ensures these costs are passed into the value of calls just as they are passed into the basis of futures over cash in any forward market.

Volatility

The inputs to the Black Scholes pricing formula are:

  • stock price
  • strike price
  • DTE (as fraction of a year)
  • RFR
  • volatility

For a given volatility, you can compute the call value, then, without using an option model, use put/call parity identities to compute the put from the call.

Note these call and put values are generated by the same volatility. We used the vol to get the call and then computed the put.

But this workflow isn’t typical. Instead, we are usually looking at option prices from a chain with implied volatility. In other words, the workflow is inverted. Instead of inputs generating option values, we see option values and imply inputs.

Notably, implied volatility.

Implied volatility is computed by fixing the option price and letting the volatility be the unknown.

[The solution is usually computed with a simple search algo like the Newton method which starts with a guess, then iterates until you are “close enough”.]

The RFR will be fixed to compute the implied vol, but when you observe the option prices you may find that the call and put have different implied vols. Another way to interpret this:

Put/call parity is not working.

But here’s the thing — put/call parity must work. If it doesn’t “work” there’s an arbitrage.

  • If the call IV is lower than the put IV, you can do that reversal trade: buy call, sell put, short stock
  • If the call IV is greater than the put IV, you can do the conversion: sell call, buy put, buy stock

What do you think is going to happen?

You will discover that a key assumption in the formula for generating those implied vols is wrong. The strike and DTE are in the contract specs. The stock price and option prices are observable from the marketplace.

The only variable remaining is the interest rate.

You can certainly call your broker to verify the interest rate, but they won’t be able to tell you tomorrow’s rate or any day after that.

What does this mean?

If you impose the rate and the call IV > put IV, then the market’s implied rate is lower than your assumption [and vice versa].

By assuming put/call parity must hold we are saying that the IV on the call and put of the same strike must be equal. But the only release valve for this constraint is we must accept that the market-implied rate can be different from what we think it is.

This is exactly what we should do.

By measuring the market rates by assuming no-arbitrage, we can then decide if a trade is attractive given our own funding rates. If the market implied interest rate is lower than what our broker offers (ie calls look cheap and puts look expensive or said otherwise the synthetic future looks discounted), then instead of buying the stock, we can buy the synthetic.

In fact, this is what professional option desks are doing all the time — they compare their funding costs from their brokers to the market-implied funding costs. If they can “refinance” their position in the options market, they effectively “go around” their broker. The implied funding market in options, including box rate markets, is often tighter than the spread of your broker’s long vs short rates. For a large enough desk it is not uncommon to have a trader whose entire job is to “manage funding” by trading rev/cons across the portfolio to reduce gross notional balances (ie if they are long lots of stock they will look to reverse or swap into futures if the cost of carry is cheaper than what the broker charges to borrow).

Solving for implied rate

Back to something we can easily see in the market — the price of the synthetic future (also known to older traders like myself as a “combo”):

Synthetic future = Intrinsic + R/C

C - P = (S-K) + R/C

I’ll use the examples from the webinar.

On 7/18/25, USO was trading $76.06

I pulled up the closest ATM strike in each month — the 76 line — and computed the synthetic future as the call – put.

I then subtract the intrinsic value of $.06 from each combo. The remainder is the R/C or cost of carry.

Remember:

We just rearrange this to solve for r, which gives us the implied rate.

Notice that the implied rates are below the Fed Funds curve at the time.

If you started with “I’m certain that the Fed Funds curve reflects my funding rate” then the combos would all look too cheap. When you “reversed” to do the arbitrage by buying the synthetic future and shorting the stock you’d discover why your Fed Funds assumption was faulty.

You will find that you are earning less than Fed Funds on your short stock proceeds.

But this gets better.

This is a perfect demonstration of why understanding this concept is immediately profitable. On 7/18, Interactive Brokers was charging 5.93% annualized to borrow USO. But you could short the stock via options to collect the rev/con instead of paying fees!

Consider the October expiry:

You could sell the synthetic futures at $.98 or $.91 more than intrinsic value, effectively collecting 3.3% annualized to be short USO instead of paying 5.93%. This is more than a 9% swing in carry costs (which is about 1/3 of the stock’s annual vol to put it in context).

Even though the funding rate from your broker stinks, you can “inherit” the market-makers rates by trading the options. The market-makers battling for arbitrage is a giant peace dividend to the rest of us who cannot access the same rates and borrow that institutions can. But even if you are a professional, the implied rates are often out of sync with the rates you can access, so there’s ample opportunity to refinance your positions in the synthetics market. The implied rate curve in the term structure is effectively an order book for a stock through time.

💡Refresher on how shorting works
 If a stock is easy to borrow, you might earn a positive rebate (e.g., SOFR – 25 bps) on collateral of short proceeds
→ If the stock is hard to borrow (high demand, low supply), the rebate can be negative. This means you pay to borrow the stock (sometimes called the borrow cost)

Discussion

It should be a revelation to realize that the physical shares market is only one price for a stock, but the derivatives markets offer many others. The USO example showed how you can short USO at a higher synthetic price than if you borrowed the shares directly. Similarly, if a synthetic future trades far below the stock price, reflecting a high borrow cost, anyone who cares to buy the stock will get a massive discount in the options market.

The “real” market

When BYND went public, the peanut gallery (ie twitter) was all screaming how they wanted to short this fake meat company, but this was a consensus view — the shares were impossible to get your hands on to short. I’m going off memory, but the options market was pricing the synthetics at about ~40% discount to the ordinary shares. So the question for the peanut gallery isn’t “Do you still want to short the shares at the market-clearing price where the stock can be both bought and sold?”

Because that price is 40% lower. And if you were a long-term bull, what are you doing buying the ordinary shares? Just take the 40% discount and buy the synthetic.

[BYND has lost most of its value since it went public 6 years ago, but I wonder if a trader who but synthetic futures and rolled the position at each expiry would have actually won. I really hope so since that would be one of my favorite case-studies on the nature of trading.]

Backtesting

Directional traders who test both long and short strategies should be using the option synthetics market to reflect tradeable prices because those prices “lock in” a funding rate. Otherwise, backtests not only require borrow rate data sets but also need to deal with the fact that borrow rates change daily. A wicked backtesting concern.

Funding all the way down

In etf fair value, I mentioned an old habit from my arb days: computing the premium/discount on an ETF before trading options on it. I’ll leave this for you to ponder:

If an ETF trades 1% above its NAV, where should the synthetics on the ETF trade?

Vol modeling

When computing option surfaces, it’s common practice to imply the rate, THEN use that rate in the implied volatility formula to compute the IVs across the skew. This ensures that each strike has a single IV, and when charting the skew, we use the implied vol from the OTM option — its mid-market willbe more reliable because of narrower bid/ask. Having a single IV per strike also ensures the absolute delta of the call and put sum to 1.

In the examples I gave above, we implied the rate from a single strike that was closest to ATM. But a more robust method would average (or weighted average) the implied rate from more than 1 strike in case the bid/ask on any single strike was shaded too much in one direction. Multiple strikes would minimize the impact of those artifacts.

Dividends

I only addressed dividends in the appendix of the prior post to keep all of this a bit easier. For our current purpose, just recall that dividends decrease the cost of carry or R/C since the call owner misses out on the dividend but still experiences the stock falling by the amount of the dividend. Meanwhile, the put owner forgoes owing the dividend on the counterfactual short shares position and benefits from the stock falling by the amount of the dividend when it “goes ex”.

→The rev/con falls pushing puts up relative to calls

Easy enough.

However, the idea of an implied rate gets more complicated when we solve for r in the presence of dividends. Although it’s not hard to understand conceptually.

Consider a situation where Fed Funds (I’ve been using FF and SOFR interchangeably), is 4%, we expect the stock pays a 1% dividend, but the rev/con is 2.5% instead of something closer to 3% that we would predict from the general shortcut of cost of carry is interest – dividends.

Is this because the options market is saying your short rebate is 50 bps less than Fed Funds OR the stock’s dividend is expected to be 50 bps more than it has been in the past OR some blend of a dividend increase and rebate difference?

Do you see how incorrect assumptions here change the implied rate, which in turn affects all the implied vols?

Not only is there an implied rate, but an implied dividend. Whenever we get multiple unknowns, we need multiple lenses to triangulate. This is the realm of quantitative vol surface modeling, a task that many professional option traders outsource to specialty firms especially if their trading must discern the value of a penny in the premium.


This concludes the 2-part series on options as funding markets. As I said in part 1, this topic represents the largest gap between what people know and what they should know about options. It affects pricing, it’s highly actionable, and by allowing anyone to “refinance” a position at professional rates, it stands as one of the easiest win-wins in trading.

how overconfidence and confirmation bias create reinforcing loops

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

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

Confidence Test

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

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

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