(taken from the thetagang sub wiki)
/r/thetagang is a sub for traders who are interested in selling options.
Options are derivative financial instruments, which means they derive their value from an underlying, such a stock or commodity. Options are a contract in which the buyer has the right but not the obligation to buy or sell the underlying at an agreed upon price on or by a certain date.
All options have an expiration date after which they stop trading. Because they eventually expire they are also wasting assets, which means they lose extrinsic value as time passes. This is where theta gang comes in.
Uh huh… I don’t really understand anything you just said, but I’m curious, why would anyone want to trade options?
There are two main reason why someone would want to trade options: hedging and speculation.
Consider an investor who buys a stock but is worried about a price decline. They can purchase options (put contracts) to protect themselves if the stock’s price were to fall. And if they think a stock is overvalued and want to short it, they can purchase options (call contracts) to protect them should the price rise. In both cases the investor is hedging their trade because they are trying to profit from the stock and not the options.
The other reason is speculation. Options allow someone to make a directional bet on a stock without buying or selling the actual stock (the underlying).
Leverage. The contract unit of an option is the amount of the underlying that the owner can buy or sell when exercised. Equity option contracts are standardized and each contract (also called a “lot”) is for 100 shares. It’s a way to have exposure to the underlying without needing the capital to buy or sell 100 shares for each contract. In other words a smaller amount of money controls a higher valued asset.
Options allow a buyer to make amazing profits. If a trade goes incredibly well, they could see profits anywhere from 100% to 10,000% (a few are even lucky enough to get 100,000%). And despite being leveraged the most amount of money they can lose is what they paid to buy the options. This is known as the premium and is paid to the seller.
The option buyer’s losses are limited to the premium and their profits are potentially unlimited, whereas for the seller the losses are potentially unlimited and the profits are limited to the premium.
WHAT?!? Why on Earth would anyone sell options with a payout like that? Especially when you could become rich so easily?
If only it were that simple.
The reality is most options expire worthless. If you buy options not only do you have to get the directional bet right, but you have to get the timing right as well.
If you buy a stock and it goes nowhere for a while and then suddenly takes off in price, you make money from this trade. Not necessarily for options. They eventually expire and if the stock soars after the option expires, tough luck. You get nothing and lose all your money.
All of the incredible gains you see with options happen because the underlying made a huge move in a relatively short period. In other words, you have to take an immense amount of risk to make a boatload of money. It’s far more likely that the options expire worthless and you lose everything.
And if getting the direction and timing right wasn’t hard enough, it gets even worse. Options are priced to lose. Recall that options are a wasting asset. An option slowly loses extrinsic value as time passes. This is referred to as theta decay. If the underlying doesn’t move in price fast enough (in the right direction, of course) to offset the loss in theta, you lose money.
This leads to an interesting outcome: an options buyer can be right and still lose money, and an options seller can be wrong and still make money.
The value an option has can be split into two parts: intrinsic and extrinsic.
Remember how options have an agreed upon price to trade the underlying at? That’s called the strike price. As an example, if a call option has a strike of $10, and the stock is trading at $10.50, the option has $0.50 of intrinsic value.
The extrinsic value is also known as the time value of an option. It’s the risk premium the seller receives for taking on the risk of selling options. Using the same example as earlier, if the option is trading for $1.10, the extrinsic value is $0.60.
The intrinsic and extrinsic value combined are the option’s premium, and the seller receives this premium in full. So if at the date of the option’s expiration the stock is trading at $10.70, the option is worth $0.70. The seller’s $0.40 profit is the buyer’s loss. And if the underlying is at $10 or less on expiration? It expires worthless and the buyer loses 100%.
This sounds too good to be true. If most options expire worthless why doesn’t everyone sell options and get rich?
If only it were that simple.
It’s true options are priced to lose and that most expire worthless. What is a wasting asset for the buyer is a wasting liability for the seller. However, it’s still a liability and sometimes that liability can end up being a real loser.
It’s not just a matter of a win/loss ratio. The magnitude of the wins vs. losses must be considered. The most an option seller can make is the premium, but they can lose far more than that if the underlying moves against them. It’s possible for a seller’s loss to be multiples of the premium they received for selling an option. If an option seller is really unfortunate, they can experience a loss on a single trade that wipes out months of profits.
There’s no easy money to be made trading options.
This section is a brief overview of the Greeks with an emphasis on the seller’s perspective.
Delta has multiple meanings:
- How much the option’s price changes relative to a change in the underlying’s price.
- The option’s equivalent of a position in the underlying (a directional bet).
- The probability the option expires in-the-money (moneyness describes the relationship between the strike price and the underlying’s spot price, or the distance between spot and strike).
Definition #2 is important to understand when making delta neutral bets (discussed later). These profit from a decrease in volatility along with collecting theta. It’s possible to construct a trade where a movement in the underlying does not change the position’s value (or by much).
Definition #3 is an approximation. Many option sellers like to sell out-of-the-money options with a delta of 0.30, which means they have an approximately 30% chance of expiring ITM.
Delta is not a constant. An option’s delta changes as the underlying’s price changes. Gamma measures how much delta changes relative to a change in the underlying’s price. Option buyers have positive gamma, whereas sellers have negative gamma.
Gamma is highest at-the-money. As expiration approaches gamma increases for ATM options and decreases for ITM and OTM options. On expiration day gamma can cause delta to rapidly change from zero to one (or zero to minus one) and vice versa for ATM options, since there’s very little time left to expire ITM.
Gamma is also affected by volatility. Options with higher volatility have lower gamma ATM, and ITM and OTM strikes have higher gamma compared to ITM and OTM strikes of options with lower volatility.
Long (positive) gamma works in favor of the buyer. As the underlying moves further ITM, gamma increases delta and profits accelerate. As the underlying moves further out-of-the-money, gamma decreases delta and losses decelerate.
Short (negative) gamma works against the seller. As the underlying moves further ITM, gamma increases delta and losses accelerate. As the underlying moves further OTM, gamma decreases delta and profits decelerate.
Gamma is bad news for sellers. Theta gang has always been at war with gamma gang. Gamma is also the reason that delta hedging is so difficult when it comes to being delta neutral.
Beloved theta. The namesake of /r/thetagang. It’s why we’re here all here and why you’re reading this.
Theta represents the time value of an option. It’s the extrinsic value of an option, and as each day ticks away the time value decreases a little. That amount is determined by theta. Theta decay is nonlinear and accelerates as expiration approaches for ATM options. ITM and OTM theta decay tends to be more linear.
The goal of an option seller is to profit from collecting theta. One could sell an option that’s ITM and profit from the underlying moving OTM, but that’s not a theta bet, that’s a directional bet. ITM options also have less time value than ATM options. ATM options have the most time value and so the most theta to collect, but are at a greater risk of expiring ITM compared to OTM options.
The more days to expiration an option has the slower the theta decay. 30-45 DTE is a very popular period to sell. Others prefer weeklies.
Vega measures how much an option’s price changes relative to a change in implied volatility. Vega is highest for ATM options and decreases the further strike prices are from the underlying’s price. The more DTE an option has the greater the vega.
The IV of an option is the market’s estimate of how volatile the underlying will be in the future. The higher the IV the greater the time value of an option, which means options with higher IVs are more expensive. Option buyers want to buy when volatility is low because options are cheaper. Sellers want to sell when volatility is high because options are more expensive.
The best time to sell options is during the gut-wrenching periods when no one wants to sell because volatility is so high (such as the March 2020 crash). Options become extremely expensive and there are juicy premiums to collect. Look for large spikes in IV.
Vomma (or volga, either term being a portmanteau for volatility gamma) is a much lesser known Greek (and also not nearly as important as the others). It measures how much an option’s vega changes as the implied volatility changes.
OTM options have the most vomma. This detail will be discussed later in a horror story of option selling gone wrong.
Rho measures how much an option’s price changes as the risk-free interest rate changes.
No one cares about rho anymore thanks to interest rates being stuck at rock bottom for over a decade.
Both option buyers and sellers care about volatility (at least they should). Buyers want to purchase when IV is low and sellers want to sell when IV is high.
An option’s IV in isolation does not actually tell you if IV is high or low. It must be compared to the historical IV for that option. Two popular methods are IV rank and IV percentile.
For example, if options on XYZ have an IV of 35% and options on ABC have an IV of 45%, on the surface ABC has higher IV. But if XYZ has an IV rank of 75% and ABC only 40%, XYZ’s IV is actually higher relative to its historical IV and may be better suited for selling.
There are different ways of measuring volatility and it’s important to not mix them up:
- Historical volatility: This is how volatile the underlying actually was. It doesn’t tell you anything about the future volatility of the underlying. This is also called realized volatility.
- Implied volatility: This is the market’s prediction of how volatile the underlying will be in the future. It could be greater than, less than, or about the same as the historical volatility. It’s only an estimate and can easily be wrong.
- Historical implied volatility: This is simply the IV of an option over time. When you’re looking at historical data and overlay HV with HIV, you can see how right or wrong the market was estimating future volatility.
- Implied volatility rank : IV rank tells you how high or low current IV is relative to HIV. It’s calculated over a period of 52 weeks. The formula is 100 * (current IV - 52 week low IV) / (52 week high IV - 52 week low IV).
- Implied volatility percentile: This tells you the percentage of time HIV has been lower than current IV. The formula is # of days with lower IV than today / # of trading days in a year (252 is normally used).
To understand what volatility skew is we have to go back to the 1970s.
You may have heard of a theoretical options pricing model called the Black-Scholes or Black-Scholes-Merton model. This model was published in 1973 and became very popular. It was widely adopted in the options market.
The original Black-Scholes model predicts that the IV curve is flat among the various strike prices with the same expiration. It didn’t matter if the strike price was OTM, ATM, or ITM, they all had the same IV.
IV stayed this way until the stock market crash of 1987, where the DJIA dropped 22.6% in a single day. This single event changed the options market forever. The IV curve was no longer flat but instead demonstrated a volatility smile (conceptual graph). Strike prices further from ATM started trading at higher IVs, resulting in a vertical skew.
The crash was a gut punch to investors that taught them extreme moves in markets were more common than you would expect, and options started being priced accordingly. But the volatility smile is not symmetrical, it’s actually skewed.
OTM puts have a higher IV than OTM calls. This is due to markets falling much faster than they rise (they take the escalator up and the elevator down). This causes more demand for OTM puts to protect long portfolio positions. Most investors are long the market, and some will sell covered calls which increases the supply for OTM calls.
Note that this is true for equity markets. Commodity markets behave differently. Normally there is a floor in commodity prices (although for commodities with storage or delivery constraints, as we learned in April 2020 they can dip below zero) and IV is higher for OTM calls compared to puts, because commodities can suddenly spike in price due to supply-side shocks.
In equity markets IV is inversely correlated with price, that is, IV rises when prices fall (reverse or negative skew). This isn’t necessarily true for commodities where rising prices can mean an increase in IV (forward or positive skew). Stated more generally, if lower strikes have higher IVs they have reverse (or negative) skew, and if higher strikes have higher IVs they have forward (or positive) skew.
There is also a horizontal skew, which means that for a given strike price, there can be different IVs depending on the expiration date. This is the term structure of volatility and can be plotted on a graph. If the curve is upward sloping (short-term has lower IV than long-term), then it’s expected that IV will rise over time (short-term IV rising) and it’s typically a bull market. If the curve is downward sloping (short-term has higher IV than long-term), then it’s expected that IV will fall over time (short-term IV falling) and it’s typically a bear market.
The story of James “Rogue Wave” Cordier of OptionSellers.com: A tragic lesson in how not to sell options
James Cordier is a former money manager who has the dubious honor of not only losing all the money of his clients by selling options, but even leaving them with a debt because the losses were so staggering.
James was a proponent of selling options and had even written a book about it. He had a now defunct website, OptionSellers.com, which targeted individuals with a high net worth. His strategy was simple: he was selling naked options on crude oil and natural gas. For years he made he made his clients plenty of money. Things were great. Until they weren’t… and the results were catastrophic. His clients lost everything and even owed money to their broker, INTL FCStone. Where did James go so wrong?
James was selling naked strangles on natural gas and crude oil. In November 2018, both markets moved against him, but the real losses came from his naked natgas calls. He sent an email with the subject line “Catastrophic Loss Event” to his clients on November 15th, dropping the bombshell that not only was all their money gone, but they may be facing a negative balance.
If you look at a chart of natgas you can see why his accounts blew up. Natgas experienced a huge spike in November and his broker liquidated their positions at an absolutely massive loss.
What mistakes did he make and what can we learn from them?
Part of his strategy involved selling deep OTM naked calls on natgas (call leg of short strangles). Deep OTM options typically don’t sell for very much, so in order to collect more money you sell a bunch of them to make it worth the trade.
This is a terrible idea and no one should ever sell a bunch of deep OTM naked options. It can work great for years, until one day it blows up your account. In order to collect a decent premium you have to overleverage yourself. This is extremely risky and you will eventually experience a major loss one day. The odds are not in your favor.
The underlying does not even need to cross the strike price for you to lose money. The underlying’s price simply needs to move significantly closer to the strike price and you’ll be deep in the red. This is made even worse if volatility spikes, which increases the option’s price and your losses (discussed in detail in the next point).
Notice what happened the following months: natgas prices crashed back to what they were before the spike. Had James not overleveraged his positions, he could’ve ridden the losses out to a profit. In fact, all those options probably would’ve expired worthless.
There is another reason not to sell many deep OTM naked options. Imagine you’re a speculator with a small account (e.g., /r/wallstreetbets). They want to trade but they can’t afford to buy ATM or slightly OTM options, so what do they do? Buy deep OTM options, bidding the price up. When a market moves big and the small-time speculators want to trade it, all they can afford are the cheap options, which are deep OTM. This is bad news when you’re short them.
Recall that for commodities volatility can be positively correlated with price. Natgas is one such commodity, and when the price spiked so did volatility. James did not understand the consequences of this.
When you are short options, you have negative vega. Volatility spiked alongside with price, and the short vega position piled up his losses in addition to being short delta.
But vega is not a constant. We finally get to discuss vomma now. Vomma measures how much an option’s vega changes as IV changes. In other words, as IV increases, so does vega thanks to vomma. Remember which options have the highest vomma? That’s right, OTM. So as IV increased, not only did his losses increase due to rising IV, but vega itself started increasing thanks to vomma, further accelerating his losses.
He got wrecked four different ways: being on the wrong side of delta, gamma adding to delta, being on the wrong side of vega, and vomma adding to vega.
Risk management is essential when it comes to trading, and selling options is no exception. Selling naked options can expose you to extreme risks, and to ignore it is simply reckless. It’s more important to avoid a huge loss than to make a huge profit, because all it takes is one big loss on a trade to make recovering from it impossible, ending your career in theta gang.
Tail risk is a very real concern in trading, and those “rare” events actually happen more frequently than traders expect (fat tails). Look at a price chart of natgas over the past twenty years. You can see random spikes sprinkled throughout the chart. James never stopped to think, what would happen to the value of my positions if natgas were to suddenly spike in price, which I know has happened in the past, and will happen again someday? How could I protect myself against this scenario?
It’s pretty obvious that if a one-day or even few weeks move manages to blow up your account and completely undo years of profits, you have zero risk management in place. This stems from not understanding how the natgas market works, and trading it with no regard to risk.
Selling naked calls on natgas is a terrible strategy because natgas can have sudden price spikes, and IV will spike with it. A much better strategy would’ve been selling a call backspread. You sell an ATM or OTM call, and you buy two or more calls that are further OTM. That way if natgas did spike your losses are limited, and you might even turn a profit on the spike.
Spend the time necessary to learn about the underlying. And don’t neglect risk management. If you’re going to sell options, you absolutely must understand how the underlying behaves and its relationship with volatility, otherwise you cannot have proper risk controls in place.
The most popular would be covered calls and cash secured puts.
CCs involve selling OTM calls on a stock you own. The short call position is covered by owning the underlying, hence the name (opposite of naked). A single equity options contract is for 100 shares, so an investor sells one call for every 100 shares they own. If the stock price rises beyond the strike price, the seller keeps the premium, but the options will get exercised and the shares called away. They sell them at the strike price, missing out on the extra gains beyond the strike. The seller still makes money on the sale, just not as much as they would have if they sold them at market price. If the stock grinds sideways, the options expire worthless. And if the stock falls in price, the options will also expire worthless, but the seller will lose money on their long stock position. Chances are they will lose more money than the premium they collected from selling the CCs.
A CSP is a naked put that’s sold either ATM or OTM with enough money in the account to cover the stock purchase if the option gets exercised. If the stock grinds sideways or rises in price, the puts expire worthless. However, if the stock falls in price the options will get exercised, and the seller will be forced to buy the stock from the options buyer at the strike price, most likely suffering a loss greater than the premium they received.
A CC has the same downside risk as a naked put. If the stock declines in either scenario the investor risks losing far more money than the premium received. If you are comfortable with the risk of selling CCs you should also be comfortable with the risk of selling CSPs. However, you can lose more money in the CSP scenario if you buy back the put before expiration if IV rises enough, vs. holding it to expiration.
Selling a CSP always means selling a naked put. It is not a covered put because you have cash to buy the stock. Whether or not you have enough money in the account to buy the shares at the strike price is irrelevant. A CP means you are also short the underlying, hence it is covered. It’s the same idea as a CC, except it has unlimited risk due to there being no theoretical limit the price the stock could increase to, whereas a long stock position can’t go below zero (not a guarantee for certain commodities).