Binary Options trading scheme: Strangle and Straddle

Hi all, I posted a thread back a few months ago when I started getting seriously back into trading after 20 years away. I thought I'd post an update with some notes on how I'm progressing. I like to type, so settle in. Maybe it'll help new traders who are exactly where I was 2 months ago, I dunno. Or maybe you'll wonder why you spent 3 minutes reading this. Risk/reward, yo.
I'm trading 5k on TastyWorks. I'm a newcomer to theta positive strategies and have done about two thirds of my overall trades in this style. However, most of my experience in trading in the past has been intraday timeframe oriented chart reading and momentum stuff. I learned almost everything "new" that I'm doing from TastyTrade, /options, /thetagang, and Option Alpha. I've enjoyed the material coming from esinvests YouTube channel quite a bit as well. The theta gang type strategies I've done have been almost entirely around binary event IV contraction (mostly earnings, but not always) and in most cases, capped to about $250 in risk per position.
The raw numbers:
Net PnL : +247
Commissions paid: -155
Fees: -42
Right away what jumps out is something that was indicated by realdeal43 and PapaCharlie9 in my previous thread. This is a tough, grindy way to trade a small account. It reminds me a little bit of when I was rising through the stakes in online poker, playing $2/4 limit holdem. Even if you're a profitable player in that game, beating the rake over the long term is very, very hard. Here, over 3 months of trading a conservative style with mostly defined risk strategies, my commissions are roughly equal to my net PnL. That is just insane, and I don't even think I've been overtrading.
55 trades total, win rate of 60%

• 33 purely directional trades - 57.5% win
• 18 long call or long put positions, +692, 55% win
• 15 call or put verticals, -121, 60% win

22 neutral / other trades

• 13 iron condors, +345, 77% win rate
• 7 strangles, -163, 71% win rate
• 1 straddle, -310, 0% win rate
• 1 butterfly, -83, 0% win rate

Biggest wins:

• PTON call purchased and held through earnings, sold the morning of announcement +410
• Trading the range on the daily chart in GLD from 158 up to 165, a mix of various calls +245
• NKLA 30 put purchased before the close on the day it went north of 100, just a pure fade +215

Biggest losses:

• EWZ 22/26 strangle that I held just way too long as it beat me up day after day from May 20-Jun 3, -316
• ZM pre earnings vertical, fading another 2 SD move (the day it hit 200 for the first time). Was expecting a post-earnings selloff given the magnitude of the up move. Stock basically hasn't had a down tick since. Max loss -247
• EWW 29 straddle, put on around the same time as the EWZ strangle. Rolled from Jun to Jul to no avail. Out at a -310 loss.

This is pretty much where I expected to be while learning a bunch of new trading techniques. And no, this is not a large sample size so I have no idea whether or not I can be profitable trading this way (yet). I am heartened by the fact that I seem to be hitting my earnings trades and selling quick spikes in IV (like weed cures Corona day). I'm disheartened that I've went against my principles several times, holding trades for longer than I originally intended, or letting losses mount, believing that I could roll or manage my way out of trouble.
I still feel like I am going against my nature to some degree. My trading in years past was scalping oriented and simple. I was taught that a good trade was right almost immediately. If it went against me, I'd cut it immediately and look for a better entry. This is absolutely nothing like that. A good trade may take weeks to develop. It's been really hard for me to sit through the troughs and it's been even harder to watch an okay profit get taken out by a big swing in delta. Part of me wonders if I am cut out for this style at all and if I shouldn't just take my 5k and start trading micro futures. But that's a different post...
I'll share a couple of my meager learnings:
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• Larger bid/ask spreads make it almost impossible to trade the higher priced names, even if you have a correct assumption. I have traded some bigger underlyings during this time like LULU and NVDA. They are just tough fills, both getting in and getting out. I almost want to say that you shouldn't even bother trading underlyings bigger than a 10 cent bid/ask spread with a small account.
• Get an idea of the timeframe you're interested in holding before putting anything on. Have a plan for entering and exiting everything that goes beyond "I'll take this trade off at 50%". You can use TA, you can use a news catalyst, a binary event, just have something. Countless sources out there talk about trading a plan. It doesn't have to be the perfect plan, it just has to be "a" plan.
• Undefined risk trades in tiny accounts need hard stops. Yes, some of the studies say that you'll do better without having fixed stop loss rules (50% of max loss, 100% of max loss) -- but what the studies don't say is the effect that it will have on you, mentally. I got pretty bent out of shape over how badly EWZ and EWW went against me -- much more than I expected. It made no sense, as I've lost way more on the turn of a card in .5 seconds and been unfazed. I was unprepared for the mental toll that it took waking up day after day, watching positions move further and further against me. Great time to be short calls during the mother of all rallies.
• My initial plan for undefined risk trades in my account was that I would only do them in ETFs. Logic being that I'm just not going to wake up to an accounting scandal or a buyout and take a $1k loss on the chin. I later expanded my range into lower priced underlyings like BBBY, TLRY, and yes, AAL. But these ETFs can and do move (I learned the hard way) and can soak up a surprising amount of BP. It might be better to have 5 iron condors taking up $1000 of BP @ 200 each instead of 2 strangles @ 500 each.

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My new questions :
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• My big wins felt like I simply leaned on my TA background or got lucky. My big losses, I sure felt like I earned those, through mistakes I've definitely since identified. The stuff in the middle, I'm just not sure. I'm up money, but it feels like I'm just spinning my wheels. My win rate is good, but I still struggle with expectations about how quickly a trade should progress. What is the next step of the process for a newer options trader? I've read some stuff on narrower spreads + more contracts vs. wider spreads and fewer contracts. Is there a number where I should just keep doing what I'm doing until I reach a specific # of occurrences? Should I even think about branching out into different strategies yet (ratio spreads, jade lizards, etc) or continue to work on these basics?
• I still feel like I am super weak in delta management. In some cases I feel like I've taken a loss simply because I didn't know what the proper management techniques were. I understand the concept of rolling out in time for a credit, but I just don't think it's in my nature to hold trades for longer than a month, and even that is hard for me. At what delta is it appropriate to start thinking about hedging?
• Every time I put on a credit spread for a 2-3 day move and am directionally correct, I often wish that I had just bought a naked option. I've caught several big moves this way in things like AAPL; most recently I bought the FB dip to the 50 day MA around 215 and took it off today at 225 (which was always my plan) -- it leads me to wonder if my expectations for credit spreads are completely out of line. I can't lie, it feels bad to catch a 10 point move and only make $40, haha. What is the ideal timeframe for a credit spread to be left on? Is it better to just buy premium with a stop loss and have a more profitable risk/reward equation for situations like the above where the only intent is to hold for a couple days?
• Here's a random question -- other than when the BPR hit is too much (ie names over $50) for undefined risk, would you rather hold 1) a strangle for 10-14 days or 2) an iron condor for 25-30 days? So far my criteria for IC vs strangle has largely been driven by the risk profile and BPR and not so much profit potential in X number of days. If you're collecting the standard 1/3rd on the IC and taking the trade off at 50% (if you're lucky) , it seems like it takes about a month to get there, most of the time.

That's enough of this wall of text for now. If you made it this far, I salute you, because this shit was even longer than my last post.

Congratulations! You are a bag holder of company XYZ which was thought to be the best penny stock ever. Instead of feeling sorry, you consider selling covered calls to help reduce your cost basis - and eventually get out of your bags with minimal loss or even a profit!
First - let's review the call option contract. The holder of the call option contract has the right but not the obligation to purchase 100 shares of XYZ at the strike price per share. This contract has an expiration date. We assume American style option contracts which means that the option can be exercised at any point prior to expiration. Thus, there are three parameters to the option contract - the strike price, the expiration date and the premium - which represents the price per share of the contract.
The holder of the call option contract is the person that buys the option. The writer of the contract is the seller. The buyer (or holder) pays the premium. The seller (or writer) collects the premium.
As an XYZ bag holder, the covered call may help. By writing a call contract against your XYZ shares, you can collect premium to reduce your investment cost in XYZ - reducing your average cost per share. For every 100 shares of XYZ, you can write 1 call contract. Notice that that by selling the contract, you do not control if the call is exercised - only the holder of the contract can exercise it.
There are several online descriptions about the covered call strategy. Here is an example that might be useful to review Covered Call Description
The general guidance is to select the call strike at the price in which you would be happy selling your shares. However, the context of most online resources on the covered call strategy assume that you either just purchased the shares at market value or your average cost is below the market price. In the case as a bag holder, your average cost is most likely over - if not significantly over - the current market price. This situation simply means that you have a little work to reduce your average before you are ready to have your bags called away. For example, you would not want to have your strike set at $2.50 when your average is above that value as this would guarantee a net loss. (However, if you are simply trying to rid your bags and your average is slightly above the strike, then you might consider it as the strike price).
One more abstract concept before getting to what you want to know. The following link shows the Profit/Loss Diagram for Covered Call Conceptually, the blue line shows the profit/loss value of your long stock position. The line crosses the x-axis at your average cost, i.e the break-even point for the long stock position. The green/red hockey stick is the profit (green) or loss (red) of the covered call position (100 long stock + 1 short call option). The profit has a maximum value at the strike price. This plateau is due to the fact that you only receive the agreed upon strike price per share when the call option is exercised. Below the strike, the profit decreases along the unit slope line until the value becomes negative. It is a misnomer to say that the covered call is at 'loss' since it is really the long stock that has decreased in value - but it is not loss (yet). Note that the break-even point marked in the plot is simply the reduced averaged cost from the collected premium selling the covered call.
As a bag holder, it will be a two-stage process: (1) reduce the average cost (2) get rid of bags.
Okay let's talk selecting strike and expiration. You must jointly select these two parameters. Far OTM strikes will collect less premium where the premium will increase as you move the strike closer to the share price. Shorter DTE will also collect less premium where the premium will increase as you increase the DTE.
It is easier to describe stage 2 "get rid of bags" first. Let us pretend that our hypothetical bag of 100 XYZ shares cost us $5.15/share. The current XYZ market price is $3/share - our hole is $2.15/share that we need to dig out. Finally, assume the following option chain (all hypothetical):

DTE	Strike	Premium	Intrinsic Value	Time Value
20	$2.5	$0.60	$0.50	$0.10
20	$5.0	$0.25	$0	$0.25
20	$7.5	$0.05	$0	$0.05
50	$2.5	$0.80	$0.50	$0.30
50	$5.0	$0.40	$0	$0.40
50	$7.5	$0.20	$0	$0.20
110	$2.5	$0.95	$0.50	$0.45
110	$5.0	$0.50	$0	$0.50
110	$7.5	$0.25	$0	$0.25

Purely made up the numbers, but the table illustrates the notional behavior of an option chain. The option value (premium) is the intrinsic value plus the time value. Only the $2.5 strike has intrinsic value since the share price is $3 (which is greater than $2.5). Notice that intrinsic value cannot be negative. The rest of the premium is the time value of the option which is essentially the monetary bet associated with the probability that the share price will exceed the strike at expiration.
According to the table, we could collect the most premium by selling the 110 DTE $2.5 call for $0.95. However, there is a couple problems with that option contract. We are sitting with bags at $5.15/share and receiving $0.95 will only reduce our average to $4.20/share. On expiration, if still above $2.5, then we are assigned, shares called away and we receive $2.50/share or a loss of $170 - not good.
Well, then how about the $5 strike at 110 DTE for $0.50? This reduces us to $4.65/share which is under the $5 strike so we would make a profit of $35! This is true - however 110 days is a long time to make $35. You might say that is fine you just want to get the bags gone don't care. Well maybe consider a shorter DTE - even the 20 DTE or 50 DTE would collect premium that reduces your average below $5. This would allow you to react to any stock movement that occurs in the near-term.
Consider person A sells the 110 DTE $5 call and person B sells the 50 DTE $5 call. Suppose that the XYZ stock increases to $4.95/share in 50 days then goes to $8 in the next 30 days then drops to $3 after another 30 days. This timeline goes 110 days and person A had to watch the price go up and fall back to the same spot with XYZ stock at $3/share. Granted the premium collected reduced the average but stilling hold the bags. Person B on the other hand has the call expire worthless when XYZ is at $4.95/share. A decision can be made - sell immediately, sell another $5 call or sell a $7.5 call. Suppose the $7.5 call is sold with 30 DTE collecting some premium, then - jackpot - the shares are called away when XYZ is trading at $8/share! Of course, no one can predict the future, but the shorter DTE enables more decision points.
The takeaway for the second step in the 2-stage approach is that you need to select your profit target to help guide your strike selection. In this example, are you happy with the XYZ shares called away at $5/share or do you want $7.5/share? What is your opinion on the stock price trajectory? When do you foresee decision points? This will help determine the strike/expiration that matches your thoughts. Note: studies have shown that actively managing your position results in better performance than simply waiting for expiration, so you can adjust the position if your assessment on the movement is incorrect.
Let's circle back to the first step "reduce the average cost". What if your average cost of your 100 shares of XYZ is $8/share? Clearly, all of the strikes in our example option chain above is "bad" to a certain extent since we would stand to lose a lot of money if the option contract is exercised. However, by describing the second step, we know the objective for this first step is to reduce our average such that we can profit from the strikes. How do we achieve this objective?
It is somewhat the same process as previously described, but you need to do your homework a little more diligently. What is your forecast on the stock movement? Since $7.5 is the closest strike to your average, when do you expect XYZ to rise from $3/share to $7.5/share? Without PR, you might say never. With some PR then maybe 50/50 chance - if so, then what is the outlook for PR? What do you think the chances of going to $5/share where you could collect more premium?
Suppose that a few XYZ bag holders (all with a $8/share cost) discuss there outlook of the XYZ stock price in the next 120 days:

Person	10 days	20 days	30 days	40 days	50 days	100 days	120 days
A	$3	$3	$3	$3	$3	$4	$4
B	$4	$4	$5	$6	$7	$12	$14
C	$7	$7	$7	$7	$7	$7	$7

Person A does not seem to think much price movement will occur. This person might sell the $5 call with either 20 DTE or 50 DTE. Then upon expiration, sell another $5 call for another 20-50 DTE. Person A could keep repeating this until the average is reduced enough to move onto step-2. Of course, this approach is risky if the Person A price forecast is incorrect and the stock price goes up - which might result in assignment too soon.
Person B appears to be the most bullish of the group. This person might sell the $5 call with 20 DTE then upon expiration sell the $7.5 call. After expiration, Person B might decide to leave the shares uncovered because her homework says XYZ is going to explode and she wants to capture those gains!
Person C believes that there will be a step increase in 10 days maybe due to major PR event. This person will not have the chance to reduce the average in time to sell quickly, so first he sells a $7.5 call with 20 DTE to chip at the average. At expiration, Person C would continue to sell $7.5 calls until the average at the point where he can move onto the "get rid of bags" step.
In all causes, each person must form an opinion on the XYZ price movement. Of course, the prediction will be wrong at some level (otherwise they wouldn't be bag holders!).
The takeaway for the first step in the 2-stage approach is that you need to do your homework to better forecast the price movement to identify the correct strikes to bring down your average. The quality of the homework and the risk that you are willing to take will dedicate the speed at which you can reduce your average.
Note that if you are unfortunate to have an extremely high average per share, then you might need to consider doing the good old buy-more-shares-to-average-down. This will be the fastest way to reduce your average. If you cannot invest more money, then the approach above will still work, but it will require much more patience. Remember there is no free lunch!
Advanced note: there is another method to reduce your (high) average per share - selling cash secured puts. It is the "put version" of a cover call. Suppose that you sell a XYZ $2.5 put contract for $0.50 with 60 DTE. You collect $50 from the premium of the contract. This money is immediately in your bank and reduces your investment cost. But what did you sell? If XYZ is trading below $2.50, then you will be assigned 100 shares of XYZ at $2.50/share or $250. You own more shares, but at a price which will reduce your average further. Being cash secured, your brokerage will reserve $250 from your account when you sell the contract. In essence, you reduce your buying power by $250 and conditionally purchase the shares - you do not have them until assignment. If XYZ is greater than the strike at expiration, then your broker gives back $250 cash / buying power and you keep the premium.
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Early assignment - one concern is the chance of early assignment. The American style option contract allows the holder the opportunity to exercise the contract at any time prior to expiration. Early assignment almost never occurs. There are special cases that typically deal with dividends but most penny stocks are not in the position to hand out dividends. Aside from that, the holder would be throwing away option time value by early exercise. It possibly can handle - probably won't - it actually would be a benefit when selling covered calls as you would receive your profit more quickly!
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This post has probably gone too long! I will stop and let's discuss this matter. I will add follow-on material with some of the following topics which factors into this discussion:

• Effect of earnings / PR / binary events on the option contract - this reaction may be different than the underlying stock reaction to the event
• The Black-Scholes option pricing model allows one to understand how the premium will change - note that "all models are incorrect, but some are useful"
• The "Greeks" give you a sense about how prices change when the stock price change - Meet the Greeks video
• Position Management - when to adjust, close, or roll
• Legging position into strangles/straddles - more advanced position with higher risk / higher reward

Open to other suggestions. I'm sure there are some typos and unclear statements - I will edit as needed!
\I'm not a financial advisor. Simply helping to 'coach' people through the process. You are responsible for your decisions. Do not execute a trade that you do not understand. Ask questions if needed!**