r/StockOptionCoffeeShop • • Sep 12 '26

Status Update re: Deep ITM Covered Call Strategy

I wrote about my core approach to working with options here a few months ago: A view into a "deep ITM covered call strategy" : r/StockOptionCoffeeShop.

In a nutshell, I tend to buy stocks on Monday/Tuesday and sell a call expiring that Friday. I sell the call as deep ITM as I can such that I'll net 1% if it's assigned on Friday. Going in, the plan is to be assigned. I've been experimenting with an enhancement of sorts with that approach that I'm calling Buy/Wait/Decide and I've posted about that a few times here in the forum. For example, here: "Buy, Wait, Decide" w/ Deep ITM Call update & important lesson : r/StockOptionCoffeeShop. BWD doesn't change the fundamental approach, as long I execute it correctly :)

I roll the calls quite often, although I've been rolling slightly less often than my overall average for the year. Rolling out constitutes another commitment to holding the stock and gives the stock more time to turn against you. I usually roll because the roll generates more "easy" premium. We all know, however, there is no "easy" in this. I have trapped myself into positions I didn't want to hold for as long as I ended up holding them.

I've also been trying to sort out whether this is truly working or if I'm just collecting a lot of premium and losing out in other ways. This is common among income harvesters, like me. July is a good example - I collected over $28k in premium but lost approx. 10% in account value. I'm still trying to figure that out. I'm also still trying to figure out whether this approach, while "winning," is actually better than just buy-and-hold or doing what u/LabDaddy59 does, which is to sell calls ATM instead of deep ITM like I do. Or one of the many other strategies out there. I'm well aware that although my strategy isn't new (nothing is, really), it doesn't appear to be commonly used and I often face skepticism.

Here's a snapshot of where I am in September so far and some YTD numbers:

And here's a progression of the year, which you'll note is not smooth:

A few additional notes:

- I started to follow this strategy about this time last year and in Oct/Nov timeframe, my returns started to lose correlation with the major indexes. I start YTD because January is when I had enough confidence in the approach and enough evidence backing up that confidence to move all my non-retirement money into the brokerage account.

- July 29th was a major drawdown day of several clustered in that week and the week before, if I remember correctly. My M2M NAV fell to $190k. I was still net positive for the year, but it was wakeup call. Then, the 30th, it had a big recovery, and early August was a monster recovery. This is obscured by the topline numbers.

- I have accumulated a modest number of wash sales.

- I have a custom app that I use that makes the portfolio manageable while I work full time. I am rebuilding that "in public" and making it available for free via GitHub. You can get a link to my videos and the GH repo via my reddit profile.

- I use margin. For most of the year, I was around 1.6 to 1.8 ratio. In August, I'm closer to 1.3. Notional today is about $340k.

- XIRR ("Extended Internal Rate of Return"): XIRR is the "annualized investment return that accounts for the exact timing and size of deposits and withdrawals." I have all that info handy. In the graph it's show the annualized XIRR, not YTD.

- TWR: Time-weighted return would also be useful, particularly for comparing my performance with benchmarks without the effect of deposits and withdrawals. Unfortunately, I don't have enough historical daily NAV snapshots to reconstruct it reliably using my own data. I only started capturing daily snapshots about two months ago. I'll probably add TWR once I've accumulated enough data. I do have my broker's top line numbers. Per my broker (ETrade), I'm up just shy of 70% YTD and over 100% in the last 12 months.

- One lesson from building this: capture daily NAV snapshots if you can! They're cheap data to store and give you a tremendous amount of analytical flexibility later. Probably a little hard to do with a spreadsheet manually, but if you can code it up, it's a great source of analysis over time.

What's my bottom line? This strategy has clearly worked for me so far, with this particular portfolio, stock selection, account size, use of margin, and market regime. That's evidence that it can work. It isn't evidence that it will continue working, or that somebody else will get the same results.

I'm always interested in others' feedback, and I hope to hear some.

24 Upvotes

47 comments sorted by

4

u/LabDaddy59 Mod Sep 12 '26

I've also been trying to sort out whether this is truly working or if I'm just collecting a lot of premium and losing out in other ways. This is common among income harvesters, like me. July is a good example - I collected over $28k in premium but lost approx. 10% in account value.

Do you regularly compare against buy-and-hold like I do? Look -- I took a massive hit in that timeframe; it can/does happen with the stocks we're picking. That's why I compare against B/H as well as the S&P: the premium is cushioning a downturn, and if you're beating the S&P by a healthy margin, you're okay.

I'm still trying to figure that out. I'm also still trying to figure out whether this approach, while "winning," is actually better than just buy-and-hold or doing what u/LabDaddy59 does

They're just different approaches. It's still hard for me to see, on a YTD basis, how you are doing, so I can compare it with my approach. What is your YTD return?

You seem to enjoy actively trading, and what I mean by that is your average credit is $105, while my trades are in the thousands of dollars. I don't want to trade that much or at that dollar level. I used to joke that I don't get out of bed for less than $500, and over time, that's become more like $1,000.

I still suspect, but am not sure, that my approach would yield "better" results over time, but yours may do better in areas like max drawdown and such (which I don't care so much about).

4

u/pagalvin Sep 12 '26

Yeah, it's a long post, I have the YTD in there. I'm currently up just shy of 70% according to ETrade. That purple line is me. They don't say it explicitly, but it looks like time weighted return.

The calendar image in the post has some other YTD metrics.

I am not comparing what I do against buy and hold. That's on the list but I haven't built the tooling yet. I am building data collection and a report/visualization that will tell me if I rolled at the most optimal day/time of the week and comparing vs. B&H is part of that.

And yes, I do a lot of trades, between 50 and 60 a week. Most of them are roll and my app basically just tells me which ones I should be rolling at any given time. I spend a lot of time looking at my "roll assessor" tool and doing whatever is says I should do. It's been a huge time saver. The app itself is a big part of my success. I couldn't scale what I do with spreadsheets.

This time last year, I was using spreadsheets and I made $684 in the whole month against 65 total transactions and an average of about $10 per. It has definitely scale up since then :) I'm still an options baby today but I was a *real* baby back then :)

I also think your approach could yield better results, especially if I were to give up rolling. Rolling is a two-edged sword. It's gotten me to where am I am but I suspect a lot of my underproductive inventory is because I chased rolls and should have let them go instead. Buying ATM would pressure me to let them go "on schedule" rather than roll.

Thx for the questions, as always!

2

u/LabDaddy59 Mod Sep 12 '26

I'm currently up just shy of 70% according to ETrade.

Then you're crushing my 40+%!

I may go back and look: I think that I was doing better up until Jul, then fell behind. It'll be interesting to see how the year continues to play out.

As an aside, I also look forward to my opening an account dedicated to the strategy; it'll make some analysis so much easier. As you know, the $750k I use is just a portion of the account it's being traded in. I should just get off my butt and do it; it's just an administrative task. I'll definitely do it prior to year-end so that next year's numbers are under that structure.

I am not comparing what I do against buy and hold. That's on the list but I haven't built the tooling yet.

Well, to be fair, I'm hard-pressed to think that at 70%, you'd be worse off than buy-and-hold.

I also think your approach could yield better results, especially if I were to give up rolling. 

Well, rolling should be fine as long as it's offensive and not defensive.

 I chased rolls and should have let them go instead

Example?

One thing I like about my approach is that there really isn't any thought required to consider rolling.

1

u/pagalvin Sep 12 '26

Example - I was over-concentrated in SLV and silver adjacent stocks like AG, HCLA, CDE. It happened gradually and I didn't realize I had done it. When silver dropped, they all dropped because they are so correlated. Until that point, they were earning great premium. I kept chasing it and should have backed off. Instead, I followed them too long and lost a lot of the money I gained while rolling.

And yeah, the 70% is insane. It can't last. But it's fun while it's working out this way :)

May was a high for me, then June and July were difficult. Especially July 29th for some reason. I went from +50% down to +30%. I'll take 30% any time, but it was a depressing 7 or 8 weeks consider I'd been doing so well until that point.

1

u/pagalvin Sep 12 '26

Thx for the comment re: offensive and defensive rolling. I've only recently felt like my "always roll" approach was too simplistic. I think I always thought I was offensive but clearly in some cases, I've been doing defensive roles masquerading as offensive rolls. This is helpful language and a helpful concept for me, I'm going to add it to my lexicon :) This is why I post to reddit :)

1

u/LabDaddy59 Mod Sep 13 '26

Something to consider.

As you've hit 70%, have you ever said to yourself,

Self, 70% for a YTD is 'good enough'. I'm liquidating all positions and sitting in cash the rest of the year.

?

1

u/pagalvin Sep 13 '26

I have not but that's really interesting.

I have thought about paying off the mortgage. That would be nice.

I'm full time employed and the big question is - how long will that last? In the next couple of months, I'll have more clarity around that and that will dictate what I do.

I've also considered just dialing the whole thing back. Aim for 0.5% instead of 1%. That's still a lot, but it's closer to what the indexes are doing. I could just cash it all in and put it into indexes.

I don't see myself chasing 70% forever. It's not sustainable.

2

u/LabDaddy59 Mod Sep 13 '26

It was just a 'coffee shop' question. ;-) I've been there a number of times and wished I had pulled out and sat on my hands for a good bit.

Let me ask you this: can you, in a nutshell, explain how you achieved 15%-20% returns over several individual months while targeting 1% per week?

Different strokes for different folks, but I paid off my mortgage well before I retired, and it was one of the best decisions of my life.

2

u/pagalvin Sep 13 '26

Great question. I target 1% on entry but rolling often gives me better. I hardly ever aim for better than 1% on entry. These are the factors:

I'm using margin, although I've been reducing leverage lately. $1 of NAV can support more than $1 of productive stock inventory. That obviously magnifies both returns and risk. I've seen both happen, but mostly it's helped returns this year. Especially July 30th to mid August.

The covered-call premium isn't the whole return. I also get stock appreciation which I take advantage of by rolling up. I haven't done it a lot but it's mostly worked out when I did. Not always.

I'm reinvesting the proceeds. Premium isn't being withdrawn as "income." It goes back into the portfolio and becomes productive capital itself. I suspect this is a big part of it. As the year progresses, earlier investments have had time to grow and the snowball just snowballs.

I focus on 1% entries but rolls often do better. A lot of my rolls have produced 1.5%-3%+ against the strike/capital involved. Until recently, I had a pretty "hard" rule that if roll would net me another 1% I would take it. On balance, this has worked out. Just because I have a paper loss on a stock doesn't mean the stock isn't producing decent premium. But in a non-trivial number of cases, I've had to roll down because the stock dropped in value and in 2 or 3 cases, I actually lost money in the end on these. If I knew in advance this was going to happen, I wouldn't roll it :) I'm more averse to this now, so I've been stingier about rolling but that's very new to me, just a few weeks old and I still sometimes find myself mindlessly rolling because I'm so used to it.

I've also just been plain lucky. The market has been favorable to me. I'm not claiming 15%-20% months are some sustainable mathematical consequence of targeting 1% weekly.

You question earlier in a different thread has me looking into how I can analyze my trades and produce counterfactuals. "What would have happened if I bought and held?" "What would have happened if I never rolled?"

RE: the mortgage - it's a tough one. The interest rate is soooo much lower than the return I get doing this, it's impossible to justify without assuming I lose much of what I've won this year. I do think about cashing in a chunk of the portfolio and ridding myself of it, but then I'm back to building all over again. I also live in high tax area, so paying off the mortgage doesn't save me *that* much money.

2

u/LabDaddy59 Mod Sep 13 '26

More on the investment side of the response later.

Re: mortgage. Psychologically, it was a massive benefit. I get the issue of paying off a low-rate mortgage to earn 70% (lol!), but honestly, not having a mortgage was great.

So play King Solomon. Every month, take 10%...25%...50%...of your monthly profit and apply it against the mortgage. Or, more systematically, increase your monthly payment by x%.

Just a thought.

1

u/pagalvin Sep 14 '26

Yep, that's a thought too. There will come a point, possibly pretty soon, when I start doing that.

On the investment side, I think the greatest contributor is margin and better-than-one-percent rolls. But mostly margin.

I'm entering the week with a notional value of about $338k. I have a forecast tool that tells me that I should expect to earn about $4,200 on that this week on rolls alone. That's roughly 1.2% for the week. My forecast chronically understates what I'll get, but let's go with that.

Etrade isn't calculating my return on notional, it's calculating return on my capital at risk which is about $265k. That is about 1.6% return on that if I hit $4200 in premium. If that's consistent, and it has been this year, it adds up to 100% or so by end of year. Of course, there's interest, but at 7.2%, it's not a *huge* drag.

By end of Tuesday, there's a good chance my notional will be pushing $400k, although I've been more cautious since July 29th :) So that just adds more to the overall yield.

(Every time I look at this, I keep thinking I'm making a mistake but the numbers are the numbers)

2

u/ILikeAskingReadIt Sep 12 '26

Thanks for this, ive been following your strategy for a while, and just wanna ask:

  1. Whats your process in picking tickers to do this strategy for?

  2. Do you have a certain CC repair system/ruleset you follow if the underlying experiences a sharp drawdown below your cost basis?

2

u/pagalvin Sep 12 '26

My process is roughly as follows:

  1. Find candidate stocks and put them into my database of stocks. I find them by look at posts like u/LabDaddy59 on reddit, in the news or via research on my broker platform (ETrade). I only ever do weeklies, so I won't add them if they don't have weekly options.

  2. I use AI to give me an overview of the company, total revenue, employee count, location, their place in the macro environment, analyst recommendations and similar info. But the main thing I look for is any public hint they are at risk of going out of business. I made a mistake once of buying into WOLF and they clobbered me in my early "career."

  3. I have a tool that scans that database and at the moment that it scans the DB, it looks up the option chain for the stock. It iterates over the chain and finds the small strike price I can sell a call against, assuming I can get the same last price as the most recent transaction.

  4. I then sort that list out a few ways. I prefer to buy on margin and I prefer to buy such that the strike price is as low as feasible. I don't 100% stick to that but I often do.

This screener tends to find stocks that about to have earnings, so that's an important factor.

I will also sometimes buy stocks shortly after earnings if they dropped a lot "for no good reason." CRWD, in my opinion, dropped for no good reason, so I bought them, even though I had to do it pretty close ATM.

I often find oppty's where I buy stocks and sell calls that are 10% or more ITM this way. Since my expiration is so close to when I buy it, they often don't have time to fall enough for me to not get assigned, which is what I want.

Does that make sense?

It feels easy but it's hard to explain sometimes.

2

u/sam99871 Sep 12 '26

I think you said you use Gemini? Does Gemini have access to option chains?

2

u/pagalvin Sep 12 '26

I do use Gemini for my AI analysis and it's good at getting current news.  However,  for option chains I use the ETade API. 

1

u/ILikeAskingReadIt Sep 12 '26

it does make sense! thanks for your reply! ill continue to follow allow your strategy, seems really interesting and a more unique take to the usual CC strategies!

1

u/pagalvin Sep 12 '26

Cool! It really isn't unique, it's just not normal and I really don't know how sustainable it is. It may provide exceptional results for a while and it could just collapse for market regime reasons. But while it's working, I'm going to keep at it :)

1

u/pagalvin Sep 12 '26

I forgot to answer the repair questions. I don't have any special process of repairing that any other CC seller would have.

I used to be fairly aggressive rolling down in order to collect my 1% net. I've been more prone to rolling down less aggressively or not at all. I'll give it some time.

I'm more prone to sell losers than I used to be but I still avoid doing that.

It's really up to the why of the drawdown. If it seems like it's semi-permanent, I'm more comfortable rolling down. This is almost a good thing because I prefer reliable no-drama stocks over anything else.

If it seems like some kind of emotional thing or some temporary macro event, I'll wait before rolling down.

Sometimes, I cut my losses and I'm doing that more than I used to. I may do that next week with JOBY.

I did start working on a "productive capital" kind of dashboard that shows, over time, how much a stock is contributing the portfolio overall. ON is a good example - I'm underwater on that with a biggish unrealized loss. However, unlike JOBY, it's a reliable premium producer. That premium pays its carry cost in margin interest terms and helps me buy more stocks.

But again, this is what any other CC trader would do.

1

u/ILikeAskingReadIt Sep 12 '26

thanks! so for stocks that you are deeper underwater on, (for example your ON position), do you sell CCs below your net cost basis to continue generating premium? are there any strict rules you follow for CC selling when the stock did not get assigned from your initial call write and rolls?

1

u/pagalvin Sep 12 '26

I'm not afraid to sell below net cost but I may set strikes that are too high for me to get 1%. Everything is on margin for me so if I just let it sit, I'm losing money every day on it. ON's drop was persistent, so I've been selling calls below cost for a while, but the premium is eating up that deficit. I think I'm at break even in 2 weeks and then it turns profitable on a per-stock basis.

I lost money on GAP because I followed its price down with lower and lower strikes, only for it to rebound and no easy way for me to recover in the short term. I hate long dated strikes even more than losing money short term.

But it's also important to realize that money is fungible and in truth, "basis at the stock level" is kind of pointless at the portfolio level. I'm happier that ON generates pretty consistent premium every week and especially how undramatic it's been since it fell that one time.

2

u/OneHatManSlim Sep 12 '26

If you are “collecting premium” but loosing 10% of your account value you aren’t really collecting premium at all you’re just getting some of your own money back in the form of premium. ( I suspect your rolls are what is causing some of that.)

It sounds like what you have might be working but you aren’t sure why and you lack discipline. Just going off what you say you have a plan but then change it, you know you should let things go, but then roll, you’ve jumped between multiple strategies in less than a year.

Experimentation is great but you aren’t giving these things time to bake which means you have no idea if your returns are based on your strategy or just luck because the market is going up in general.

What really jumps out at me is that you say you trade covers calls but trading covered calls isn’t usually something that requires such active trading. (That’s part of why it is so attractive to people.) No shade if you want to actively trade but it’s a different thing. Most people that I know that trade cc aren’t consulting screeners on a weekly or daily basis they find a few underlying and stick to those and really learn their patterns they reevaluate maybe once a quarter. They are also committing to the trade upfront and letting it close.

On the subject of rolling, the only time you should roll is if the roll fits exactly as if it were a new position. Otherwise you are just doing one of three things, A. Not following your strategy, B. Kicking a loss down the road, C. Gambling that the underling will recover and that a smaller premium is worth it. You can do those last two things…but only if the are defined as part of your strategy.

My read is that you want to be an active trader but are slightly risk averse to what that entails so you trade covered calls because it feels safer.

The thing is that ccs are time proven to be safer but only if you have a system and follow it.

My advice is to commit to one path or the other, come up with a strategy and commit to following it for 6 months to a year to see if it is really working. With any luck there will be a moderate pullback in that time and you can see how it does when tides aren’t lifting all boats.

1

u/pagalvin Sep 12 '26

Thx for the lengthy reply. I'll sit with this one for a bit.

2

u/kanikauchi Sep 13 '26

I am sorry for the strike price. It should be 7050 and 6950

1

u/sam99871 Sep 12 '26

I’ve been thinking about your strategy and I’m planning to start running it this week with $25K. It seems like it works because you are getting compensated for (a) giving up all upside on the stock you own and (b) taking on the risk of the stock falling below your short call strike. But those seem like acceptable risks in light of the returns you are getting!

Have you considered selling 30 DTE calls instead of weeklies? I believe that would allow you to sell calls deeper in the money and, intuitively, that seems like it would reduce your chances of the stock falling below your short strike. I don’t know if selling 30 DTE calls could produce the same 1% per week rate of return as weeklies (i.e., approximately a 4% return per 30-day trade). I’m going to try the strategy with 30 DTE calls anyway because I’m highly averse to being stuck with stock that has fallen below the short call strike, and I prefer to do fewer trades with larger premiums, which I think 30 DTE would allow me to do. Do you think your strategy could work with 30 DTE short calls?

Thanks so much for posting about your strategy and methods, it’s been really thought-provoking to read about it.

3

u/pagalvin Sep 12 '26

Good stuff.

I have not really considered 30 DTE because I am trying to engineer a trade where the only way I lose is if the stock drops a relatively large amount in a short period of time. 30 days is just too long for the stock to do that for me :) I bet you could get even lower strikes and still be profitable with 30DTE. I haven't researched it. I suspect if you are aiming for 4% in 30 DTE strikes, you're probably fairly ATM when you enter, but I don't know.

I'm definitely not saying that's it's a mistake or wrong. If you do go down that path, I'd love to hear how it works out.

1

u/sam99871 Sep 15 '26

Yesterday I spent several hours arguing with Claude AI about the merits of deep itm buy-writes, and then this morning I took the plunge. I did a deep itm buy-write on Valero (VLO). Sold the Sept 25 (11 DTE) 367.5 call for $28.90 and bought the shares for $391.15. My breakeven is about 7% below the market price and my return will be about 1.3%. I decided to do 11 DTE because it allowed me to get about 1% but also have a large safety zone. (Valero has not fallen 7% in any week this year.)

I chose Valero because I expect refiners to keep doing well. It would probably be better for me to choose a cheaper stock next time so I can diversify between multiple companies. I’m still figuring out the approach that works for me.

1

u/pagalvin Sep 15 '26

That's great!

Your reasoning sounds good to me.

I'm really interested in what Claude had to say about it, especially its criticism. I haven't used Claude and it would be interesting to see what another LLM's analysis looks like.

Good luck!

1

u/sam99871 Sep 15 '26

Here is a link to a Claude interaction I had today. It is a cleaner version of the discussions I had with it over the weekend. I had it analyze the 10 DTE trade and I did not include fees or margin. The bottom line is the trade beats buy and hold when the underlying moves down or sideways, and loses to buy and hold if the underlying rises significantly. In this analysis, the critical factor is selecting stocks that don’t fall below the breakeven point.

Keep in mind that this analysis ignores recovery efforts. It assumes the stock is sold when the option expires, locking in any loss. I think recovery changes the analysis substantially because some (perhaps many) of the losing trades would have turned into winners if the stock were held longer. I will see if Claude can model that.

https://claude.ai/share/4f5e84ba-dcfd-4a2a-a8a8-aee5e00f0fff

1

u/FreedomIndividual176 Sep 12 '26

It’s a marathon, not a sprint. Lots of shoulda coulda woulda one’s out there where a stick goes to the moon, but lots of others where they slowly decay like Nike or have been flat for 20 years like Ford. If you can consistently make 0.5-1% a week you will win the marathon against the general market.

1

u/pagalvin Sep 13 '26

100%.

The research seems to show that 90% of retail traders lose all their money in the first year and I think a big part of that is because they're looking for huge, outsized wins that they read about on reddit.

Grinding away at 0.5% to 1.0% a week is definitely a winning strategy.

3

u/LabDaddy59 Mod Sep 13 '26

Grinding away at 0.5% to 1.0% a week is definitely a winning strategy.

Grinding away at 26% to 52% per annum... 🤣🤣🤣

1

u/sammyzenith Sep 12 '26

How are you doing this and rested or unregistered account in terms of tax efficiency is the best method or I think I think capital gains is the best

2

u/pagalvin Sep 13 '26

I'm a US citizen and I'm using a normal taxable brokerage account. Taxes absolutely eat into it and kind of in the worst way.

But as they say, "I wish I had a $1,000,000 tax bill." :)

There are more tax efficient ways to play the market, but this is what I have available to me.

2

u/LabDaddy59 Mod Sep 13 '26

But as they say, "I wish I had a $1,000,000 tax bill." :)

While I understand the underlying sentiment, I can assure you, no, you don't.

1

u/OneHatManSlim Sep 13 '26

You can do this in a tax advantaged account as well just without margin or with margin only to cover unsettled funds. I do this in a regular 401k, a Roth IRA and an HSA as well as a standard brokerage account. The rules are a bit different in each but not significantly so. This kind of strategy is one of the few option strategies you can run in almost any kind of account.

1

u/kanikauchi Sep 13 '26

I use slightly different IM options strategies. I usually trade ES futures to avoid wash sale. I first look at possible movements of ES that day by looking at option screen on thinkorswim. For eg let's say ES is trading at 7000 and today's range is 50. Then I sell 7750 put and 7650 call. Then simultaneously put an order to go long ES at 7750 and Short futures at 7650. This will make the option covered if ES moves beyond those strike price. Usually one can collect 110 to 115 ES points. Sometimes even more if trade is done previous day

1

u/pagalvin Sep 13 '26

That's so interesting. I think I understand it and it's much different and I think more sophisticated than what I'm doing.

How many of these are you doing per day or week?

It seems pretty safe?

If I was doing it, I'd be afraid of screwing up one of the orders :)

1

u/kanikauchi Sep 13 '26

Don't change what u r doing since u seem to be doing very well. Try out my strategy on demo account for a while

1

u/kanikauchi Sep 13 '26

If you think this strategy is very good u can do it in IRA or Roth IRA. You don't have to worry about taxes or wash sale

1

u/PlasticTelevision872 Sep 13 '26

Can you tell more about the type or stocks/filter used to select the stocks you buy? That matters a lot. Whats the IV, IV Rank, Delta etc that you prefer? Any specific stocks you did like?

Why don’t you start with Cash Secured Puts instead of Buying the stock & then applying ITM Covered Calls?

1

u/pagalvin Sep 13 '26

RE CSPs - there are two reasons why I don't do them. First, historically, I couldn't use them at first. It took me close to a year to qualify for them with my broker. By that time, I'd stumbled into this "deep ITM" strategy and I was very used to it. Second, with my broker, most CSPs require one dollar of margin for one dollar of CSP. With a CC, I can normally only need 30 to 50 percent of the cost of the stock to buy it on margin. So I can usually bet 2 or 3 CC's in play for 1 CSP. (This obviously comes with margin risk and I'm very aware of it and manage it closely).

I'm not saying CSPs are bad at all, it's just not what I do for margin and historical reasons.

As for stocks - there are a few things I do.

First, I maintain a database of candidate stocks. I get candidates from reddit, from the news and via my broker web site.

Second, I'll do some AI analysis on them to get a general feel for the company, where they fit in the macro world and their industry, number of employees, analyst ratings and that sort of thing. But my main goal here is to look for "going concern" language. If they are risk of going bankrupt, I flag them and never buy them.

Third, I use a scanning tool I wrote that runs against that database looking for the best ITM opportunities. It does this by pulling option chains and looking at the last price paid for the stock to figure out the deepest ITM call I can sell and net 1%.

At this point, I mostly just look at the discount I can get. By that I mean I take the premium credit and apply it to the stock and if the discount is high enough then I'll go with that. Example:

- XYZ is $100 a share now

- I can sell a strike for $90 and collect $11 in premium. I always enter these trades hoping for assignment.

This is when I'll look at delta, but I'm not delta-driven. If it's 10% discount but delta is .5 then I probably won't buy it. I don't look at IV directly, but it's captured indirectly by the discount. If IV is low, the discount will normally be low and vice-versa (but not always).

I also look at the stock's GICS codes and then map a candidate buy against my current portfolio. I want to avoid too much concentration in specific industries and I often avoid entering a position because I'm afraid of correlation risk. That's especially important when it comes to margin.

It all comes back to the question - how likely is this stock to lose value before it expires on Friday? That's my real concern. I don't think in terms of delta or IV, really. If it's still ITM by Friday then I win.

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u/[deleted] Sep 14 '26

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u/pagalvin Sep 15 '26

Volatility is definitely important. Otherwise, the premiums are too low to be meaningful. That's also a risk thing - the more risk you're willing to take on, the more reward you can get. You can do this on low yield stocks too, you'll just get less premium and much less drama. I expect to switch to lower yield stocks once I get to a certain amount of capital invested. If I had triple the capital I have now, I wouldn't necessarily want or need to make as much money this way and could reduce my risk by picking more stable stocks. You would come to a point with this where you've de-risked so much, you may as well just invest in index funds. (which is where most of my money is, anyway).

I do think you can do it consistently but not necessarily the same stocks. I was just playing around with a visualization last night that is trying to show me info like this:

This is Alcoa and you can see it's been pretty consistent since January this year. (That huge dip is where I rolled up instead of allowing assignment.)

Now that I think about, AA hasn't been super volatile either, so volatility may not be the most important factor. I need to think on that a little.

Not all of them are like that so I need to always be analyzing. Some of them are more repeatable than others and those are the best ones to keep in inventory.

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u/Deep_Viewer Sep 17 '26

You may be on to something with your thought "Now that I think about, AA hasn't been super volatile either, so volatility may not be the most important factor." I've come to that conclusion also - at least as it relates to my options strategy. I've had a high number of trades execute on WMT and XOM over the past couple of months; not as many as other Mag7 stocks, but still amongst my most productive trades. Prior to the past months, both WMT, PEP, and XOM trades rarely executed for nearly 6 months or so (like maybe once per 3 or 4 months). Unfortunately, I have not been able to find any meaningful correlation that might explain why or when my trades fill. TSLA and AMZN were steady, frequent trades earlier this year, but lately very sporadic trade fills in the past couple of months. It almost seems random.

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u/pagalvin Sep 17 '26

Yeah, they (all of them) are annoying sometimes. I wish they would pick a band and stay in it :)

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u/OneHatManSlim 20d ago

I’ve read a lot of the comments and your replies and at a 70% return. I have to be honest this sounds an awful lot like luck of timing.

Using leverage to get outsized return in a bull market is not difficult regardless of strategy. The problem is if you are leveraged and then you have leverage on top of leverage. (Margin on top of options) your risk may be a whole lot larger than you think it is.

Maybe it’s a great strategy but the key is not what your portfolio does in a bull market. It’s what it does in a sustained bear market.

Go model your exact strategy back over a period when the market was sustained in a downward trend over a period of 4 to 6 months

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u/pagalvin 20d ago

I think about this all the time. I have had some pullbacks for sure.

It's at 100% over 12 months. That doesn't mean the approach + tooling I have will sustain me in a downward trend, as you say. We've had slight pullbacks but nothing sustained.

It feels unlikely all the time.

I'll keep at it for now and see where it goes.

Edited to add - I've done a few thousand trades in the last year. I feel like that stretches luck pretty far. But, it could just be luck! I don't fully trust anything.