So you want to trade options? You want to get rich quick? You want to be like that guy from Wolf of Wall Street(not Leo, every man wants to be Leo already). If you’ve answered yes to all three of these questions you’ve undoubtedly dabbled (or at least wanted to dabble) in cheap weekly options. There is no quicker way to make or lose a fortune than in high risk/high reward option plays. Below we are going to breakdown when these might be the right choice, and how to play them without blowing up your account.

Here are 4 “lotto options truths” to keep in mind before we dive in:

• First off, I don’t recommend playing these on every position, and if you do I would suggest not building yourself a portfolio full of them. While it is fun logging in to your account and seeing a 50% increase, I can assure you the opposite is not quite so fun.
• Secondly, these are typically always going to be front week plays or at most following week. What does this mean? This means that you need your move and you need it now. If there is a delay, the theta burn with eat your position alive.
• Thirdly, only risk what you are willing to lose. With the high theta burn and large gamma risk, if you get choppy price action or price action moving against your position, they will become doughnuts in the blink of an eye.
• Lastly, if the terms “Delta”, “Gamma”, “Theta”, or “Vega” are literally Greek to you, I would suggest doing a bit of studying on the mechanics of options before diving in head first. These are important terms when understanding how an option is prices, and how it will act in comparison to the underlying asset. I can do a basic review in the future, so shoot me a note if that would be worthwhile.

So if I am looking to play a high risk option, how do I go about it?  These are going to be quick plays, so MOMO, snap backs, or playing stocks for a bounce all would be decent set ups. I typically don’t play  lotto’s for earnings as they don’t offer great risk/reward in my opinion. These setups are the same whether option or common stock, but with lotto type options you can’t afford to be wrong or late. The above mentioned theta risk is inflated in lotto type plays, and this is only exacerbated by the fact that these will always start OTM or out of the money. You don’t necessarily need to get ITM or in the money to profit, but if you go the wrong way you have no safety net of any real intrinsic value attached.

After I’ve identified a stock and an expected move, you then have to take a look at the options grid and see how the different options are being priced, and what might make sense. Typically, I am looking for something with a high delta, at a realistic strike. The higher delta means that for movement in your predicted direction, you will get paid more. For example: if a call option has a delta of 1.00(sometimes noted as 100), for every $1 increase in the underlying stock, the call option will increase by $1.00 all else being equal. The other Greeks also come in to play here like gamma which will affect the rate of change in the delta, but you get the idea. So when looking at a lotto call for example, I want a high delta. Why? Because I want to get paid. These are high risk high reward remember, so if I get my move I want to get the payoff. A large majority of these will expire worthless so the winners need to win big for you. This is also where I define my risk. When you’re buying lotto plays, the chances of salvaging much of your buy in can often be low, so I will only buy what I am willing to lose outright. This helps not only curb large losses, but it also helps me manage my positions without large emotional swings. Manage your risk up front the best you can and it will go a long way towards success.

Let’s use an example from the room this week. I wanted to play $CHK for a bounce, but wasn’t too confident that I would get my move with some pending market weakness and overall choppy markets. I knew if it did bounce, it should have some legs as it recently came down hard from a swing high(good), but it had yet to break out of the bull flag pattern that I had it in(not so good). I could have waited for it to break out to the upside, but positive price movement and strength in oil lead to jumping on it now instead of waiting. If I would have waited for it to break out to the upside, I would have also likely had to move up at least a strike to get a similar set up which meant going to 8’s, and that didn’t leave me with much upside against the prior swing high of $8.20.

They don’t call them lotto’s for nothing after all! So with $CHK trading at 7.03 and 8 days to expiry or DTE, I picked up a handful of the Dec 23 7.5 calls for .11 each. You will note the large delta and gamma which means that these options will explode with positive price movement. Yes, they will also bleed out if I don’t get my move. You will also notice the small price tag attached to each contract. If these got to zero tomorrow I won’t be elated, but I won’t lose any sleep over the loss either.

Here’s what I ended up with, and you can see what I mean by keeping size small on a play like this. This was as of close on 12/15.

Here is the same position, only one day later. The interesting move, and why our position is now worth less lies in the Theta. Above we had a large theta of -16.11, and now the theta is -14.57. This is the time value, and what is working against you with short duration options. Remember my saying that you need your move and you need it now? We got a 2% move in the underlying asset, and lost money day over day because of the Theta decay. Let’s also look at the Delta which increased for two reasons. The main reason that Delta increased is that the underlying asset moved in our favor, but the Vega also moved slightly which will increase the Delta as well. This also brought the Gamma along with it and we saw a large increase there. If the underlying asset would have stayed flat day over day, we could have expected a lower Delta as the time decay would have brought it down as remember that as expiry all out of the money options have a Delta of zero.

As of now we are about even on the position, and all of the same rules apply moving forward. My typical goal for these lotto’s is to sell half of my position for a double, and let the other half “ride free” so to speak. This not only covers your costs for the initial purchase, but it also takes the pressure off and lets you manage the position knowing that you have already made your money back. I will do another post next weekend detailing how this ended up, and if $CHK brought me a present or a lump of coal for Christmas.

I hope you have a great week of trading, and send me a note in the room if this was worthwhile or if you would like to see something else discussed.

Mathew Waterfall

Twitter: https://twitter.com/quadzilla_jr