• This post is about my view on selling covered calls below the cost basis of your stock (stock purchase price) when overwriting your portfolio.
• Is it a problem or a betterment to your portfolio?
• Other implications, such as taxes.

I have seen investors expressing their concerns when the markets dropped earlier this year and now when we are seeing another 10% (and maybe even more than that) correction. Many said, that they had to sell their covered calls below their purchase price and now they are worried that if a stock goes up, they may be assigned and realize a significant loss being forced selling their position below their cost basis.

I was afraid of this event too. But, I was thinking about this and realized, that being assigned, is not such a bad thing as you may think. Let’s review my thinking process and see what roadblocks are there when selling covered calls and you have to sell below your cost basis.
 

If you are like me and try to build and accumulate your portfolio, you may have been accumulating shares of your favorite stocks when the market was all booming, everybody was optimistic, FED was raising interest rates (well, maybe not yet), the economy was rosy, someone was boasting how great job he has done and multiplied your 401k, the future was brighter and brighter every day, and you kept buying and buying your dream shares.

Then, you have reached your goal and accumulated 100 shares of your favorite stock and started selling covered calls to boost your income, so you too could boast about your investing skills.

But then, all the bright future dimmed. Actually, the future just crashed, you got sick seeing your work disappear and now, you were thinking: “What now?”
 

I had the same experience. I accumulated 100 shares of AT&T (T) and my cost basis was $31.94 (I was lucky on this one as I have another great stock which I accumulated at a lot higher cost). Today, AT&T is trading at $28.63. Looking at the options chain, there is no premium at the cost basis or above. No matter which expiration you look at, there is no premium worth taking the risk of an assignment.
 

What to do?
 

You have two options:
 
1) Do nothing, stop selling covered calls until the stock price recovers at or above your cost basis, and then you can start selling covered calls again.
Or
2) Keep selling covered calls but below your cost basis to collect a decent premium. For example, selling a 60 DTE at 30 strike can bring you 0.37 cents or 37 dollars premium. It is OK. I can take it.
 

But wait a minute. If you sell at 30 strike with a 31.94 cost basis and get assigned, you will realize a $1.94 or $194 loss! The premium will lower the loss but not much. And I do not want the loss.
 

There are again a few options you have
 
1) Try to keep rolling your calls higher and away in time. I have done that on a few positions to avoid their assignment and give the stock time to recover.
2) Close the position before it gets in the money. The closing cost will be probably less than the full loss and that may be acceptable for you.
Or
3) Let it assigned.

Once you get assigned, I usually use the proceeds to sell in the money puts. For example, I got assigned and my shares were called away at 30 a share but I immediately sold 29 in the money puts and collected 1.11 credit. If the stock stays depressed, then I get assigned and buy my 100 shares back at 29 a share. If the stock starts moving higher, I start rolling my puts higher too, collecting more credit.
 

What have I just achieved here?
 

First, I have collected a $37 credit on the original covered call.
Second, I got assigned, sold my 100 shares and realized $194 loss on the stock.
Third, I sold new in the money put and collected $111 credit.
Fourth, I lowered my original $31.94 cost basis down to a new $29 a share cost basis.
Fith, I can now sell a new covered call with 30 dollars strike, collect additional 0.40 credit and have a potential gain of $100 on the stock if I get assigned again.
 

I see this as betterment for my portfolio. For a small cost, I could “roll” my stock down, improve my position, and gain potential. And the cost I paid (about 0.46 per contract or 100 shares) was quickly offset by the new covered call sale and added potential gain on the stock which would not be possible should my original cost basis stay.
 

What’s the catch here?
 

Honestly, I do not see many (though there are a few). I actually liked the result of improving my portfolio holdings. The only issue is that you may lose a dividend if this swap of cost basis happens around the ex-dividend day and you happen to be so unlucky that you miss the dividend. In this case, it is better to buy shares outright and not using puts to buy in.

The second issue could be a taxable event. If you were called away on your stock prior to the minimum tax holding period in order to treat your sale as a long term gain and not a short term one, you may be hit with a higher income tax. Also, if you sell the stock and buy back in the position within the 30 day period, this would be treated as a wash sale and you will not be able to use the tax loss to offset your tax gains. However, my trades are small at this time that I do not worry about these events yet.
 

What about you? Are you afraid selling covered calls below your cost basis?
 

In my portfolio watch list, only a handful of stocks are good to buy in this overvalued market. The list is not yet complete, but I have time to fill in other stocks later on.

Most of the stocks are dividend aristocrats. Some lost the status many years ago yet I decided to keep them, others lost the status this year due to COVID, and I decided to keep them too as I still think they are good companies, e.g. Disney (DIS) and the dividend cut or suspension is temporary.
 

Account Net-Liq: $7,477.66
SPX value: 3,426.96
Shiller PE: 31.47
 

In my older post I wrote about the market high valuations and how you can mitigate the problem with valuation.

You hear (and read) people complaining that valuations are high and there is nothing to invest in. It is not true. And people who say that do not do their homework properly.

I must admit, that when I was writing my original post, I too made the same mistake and looked at stocks via whole market magnifying glass and ignored the reality, that the whole market doesn’t represent the stocks. It is the stocks that represent the market. Unfortunately, SPX or SPY represents only a fraction of the market and it can be easily manipulated by a few stocks. Before you start complaining about it, let me assure you, it has been like that since the inception of the aforementioned indexes. They were set up that way from the beginning and there will always be stocks that have significant weight to push SPX higher although the entire market is different.

It was the case with the recent rally. The SPX was rallying hard and many could get the impression that all stocks became expensive. Nope, it was only a few tech stocks that moved the market, others lagged.

I could see this phenomenon in my portfolio. While SPX was making new all-time highs, my portfolio net-liq was going down. It was best illustrated when you looked at the heat map back then.

This is how the S&P500 heat map looked like:
 

It is obvious what was driving the market up. Technology stocks, communications… everything else was red. It is something you would expect. People are sitting at home, doing nothing, some trading stocks at Robinhood and losing money, others using computers, like kids in schools, shopping, watching TV shows, or zoom, go-to-meeting app, or other apps to do their job (those lucky enough to have a job). Other businesses struggle.

This is how IWM, representing small caps looked like:
 

I am pointing this up to show that although the market, represented by SPX, was making new highs, not all stocks participated in this rally. And even if they did, they were still undervalued by their earnings and P/E measures.

If people really keep screaming about the market being overvalued, then they do not really look under the surface. And I must admit, I fell for this too and dismissed the entire market as overvalued meaning all stocks were overvalued.

But, they were not.

In my previous post I published the following table indicating high quality dividend aristocrats with great dividend history and highest yield among the aristocrats.
 

And I was eager to start accumulating these shares as per my original plan and once I reached 100 shares, start selling covered calls. My only defense against high valuation was selling covered calls and puts around these positions and lower my cost basis.

However, I decided to take another look at valuations when I realized that not all stocks are overvalued. Some may be valued correctly, some still undervalued, and of course some grossly overvalued.

I took another look at my previous selection and decided to add a few comparisons. My criteria for valuation were:
 

• Current P/E
• Theoretical (calculated) multiple P/E value based on market historical valuations
• Calculated intrinsic value based on earnings growth and P/E multiple
• Income generated from dividends must beat income from S&P 500
• Stock growth must beat S&P 500 growth

Based on these criteria I reviewed my previous selection once again and the result was that only two companies were undervalued and beat the market:
 

From the new table, there are two patterns I am going to follow:
 

1. All three criteria must be met, that is, the stock must be undervalued, its income and growth must beat the market.
2. It is OK to have a stock that is undervalued and its income beats the market only.

Based on these results, I will be accumulating stocks that meet all three criteria (pattern #1), and eventually, once all stocks of my interest are all accumulated, I may start accumulating stocks that meet only two criteria (pattern #2). However, the valuation of any stock must be always “green” (undervalued) in order to keep buying these shares. If a stock is overvalued, I will skip purchasing and wait for a correction or pullback to start buying.

There are stocks, though, that will always trade at high valuation (premium) no matter what. For example, Realty Income (O) was always overvalued. I checked the 20-year history of this stock and it never traded at its earnings valuation. Only once in the 20-year period, the stock pulled back to its fair value – in 2008.

The same valuation issue is with Coca Cola (KO). The stock always traded at a premium to its fair value. Waiting for it to be fairly valued, you would never buy. It only happened once when the stock pulled back to its fair value – in 2008.

These are stocks I consider high-quality stocks and I like to own them. Buying them, though, I would have to bring their valuation artificially down – using options and selling puts and covered calls.

Account Net-Liq: $7,143.75
SPX value: 3,444.02
Shiller PE: 31.58
 

Is this the end of the correction? Or just a bounce before we go back lower? If you look at today’s price action, the swing is spectacular. We have seen it in 2018 happening when the market crashed more than 2% and then ended where it started recovering more than 2%. We even have seen times when the market crashed more than 2% and recovered more than 2%, and added some! All in one day.

I have been trading for some time (since 1996) but do not recall times with such violent swings in such a short period of time. But I am old and my memory is failing me, I guess. Nevertheless, a few days long declines were typically followed by a few days long recoveries. In the past. Today, we have a one day bum, and the next day it is all gone. Just look at today’s trading chart:

Of course, the price may change before I finish writing this however, I do not expect it. We have seen a two days long correction of a 6.6% and it seems, it will be all gone today. We may not necessarily end in the green today, but next week everything will be forgotten.
 

Yesterday, I was frustrated over this price action as it was ruining my SPX trade repair efforts and now it looks like, I will be back on track fixing my early mistakes. If we start rallying again next week, I may be back in trouble on the call side.

As a reminder, last few years, I tried to actively trade SPX options, zero DTE trades, Iron Condors and strangles. I ruined my accounts. I tried to push it. I tried to study how to trade these trades and be successful. I never made it. And, I am officially admitting, that I was wrong, and maybe not as gifted as others who trade these trades successfully. I may have been undercapitalized for these types of trades or not glued to the computer monitor long enough, or not able to adjust fast enough, or whatever I was doing wrong, I never figured out how to fix a bad trade without losing money. Today, I have a few bad trades I drag around. I keep rolling them to get them into expiration without large losses and use other trades to generate income to pay for these repairs. It works so far, but in a market like this, it can be very frustrating. And, when I am done with these repairs, I will not trade these trades anymore. I am going back to my original strategy from 1996 – 2014 which worked but it was not a quick-rich scheme trading I wanted.

What to do today? Buy the dip. Because it is all it was. A great opportunity to enter into positions you may have liquidated a long time ago. Or establish new ones. Next week will be bullish again.

If you are interested to see what stocks and what options we trade, then join us at MeWe. We no longer participate at Facebook (very little though) but we are active at MeWe.

Account Net-Liq: $7,202.95
SPX value: 3,455.06
Shiller PE: 31.73
 

The market rallied and reached a 3,588.11 level. All new ATH! Outstanding rally! Unfortunately, that rally was totally unhealthy and pushed up by tech companies only. Many of my positions in all portfolios went pretty much nowhere, the only SPY was relentlessly running up and up every single day. It became frustrating at some point. The problem I got was that I was trying to repair my SPX position. With the rally, I had to raise my puts and calls higher. And, honestly, I started feeling uncomfortable with it.

So, when we crashed almost 5% today, the market sliced through my puts ruining all my effort to repair the trade and release some BP. That is more frustrating as I am running out of cash and repairing the trade was already costly.

Now, will the market drift lower? Continue the selloff? Or are we seeing a pullback that will recover in a few days? A million-dollar question. I think I will start lowering my puts until I can see where we are heading next. However, these violent moves up and then crash back down is frustrating. It diminishes all my efforts.

At least, my Boeing (BA) position which I started repairing sometimes ago is doing well. The difference between BA and SPX is that BA was falling steadily with now violent moves up or down.

If you are interested to see what stocks and what options we trade, then join us at MeWe. We no longer participate at Facebook (very little though) but we are active at MeWe.

Account Net-Liq: $7,437.20
SPX value: 3,479.73
Shiller PE: 32.01
 

I was looking for opportunities where I can store my cash in my trading account in lieu of leaving it in the account, sitting there and doing nothing.

I also didn’t want to withdraw them and save it in a savings account. That would work against my Net-Liq.

I also wanted the money to be blocked, so I couldn’t use them in other trades. I am now saving cash for another trade I want to take (buy LEAPS against SPY and start selling covered calls) and I must admit my discipline is not yet perfect and I might be tempted to use that money on another trade. So locking the cash in equity which would not lose value and even make some would be perfect.

But, where could you put your money, short term, preserve their value, and maybe make some? Make better than 0.0009 APY the broker may pay you for cash?

This is a question to savers all around the world too. If you look at the current savings accounts rates, you would want to cry!

The rates are pitiful and they may drop even lower. Poor savers! Retired people who depended on CDs or savings accounts are ruined.

I finally found a good opportunity! Thanks to another investor in a Facebook group, who pointed me to an opportunity which may do exactly what I am looking for – safety, stability, and some decent income.
 

iShares Ultra Short-Term Bond ETF (ICSH)
 

ICSH is a short term bond ETF that seems to fulfill my needs. It holds its value (slightly going up), it pays dividends (nothing extra), the yield is about 2.20% at the current price of $50.56 a share, but definitely better than today’s high yield savings accounts) and during March selloff it only lost about 4.45% while the entire market lost almost 40%. Not bad in my opinion. And, it pays a monthly dividend.

I believe, this is a good way to hold cash, or if you are afraid of the stock market, or a retiree and looking for a savings account which pays better yield (a lot better) than current high yield savings accounts, then, in my opinion, ICSH is a good option to do.

Thus, my goal is to save $4,000 in my brokerage account and then buy SPY LEAPS calls and start selling covered calls. I will be saving my cash using ICSH.

If you are interested to see what stocks and what options we trade, then join us at MeWe. We no longer participate at Facebook (very little though) but we are active at MeWe.

Account Net-Liq: $7,676.23
SPX value: 3,372.85
Shiller PE: 31.20
 

I wondered all the time whether it is better to own monthly or quarterly dividend-paying stocks. The narrative goes, that with monthly paying stocks, your dividend compounding will go faster and you get better results over time.
 

1. Well, the truth is, it doesn’t matter.
2. You will not get any better results with monthly payers than quarterly payers. The difference is so insignificant that it doesn’t justify the pitfalls of investing in monthly payers.
3. Investing in monthly payers is just psychological. All it does is that you feel better about your dividend portfolio.
4. Unfortunately, most monthly payers are in REITs, BDCs (Business Development Companies), or MLPs category, and except a few, risky and garbage not worth your money.
5. There are better ways to create monthly dividend by staging quarterly payers together. If you select high-quality dividend aristocrats, it will take just 12 stocks to create monthly dividend payments.
6. Use options to boost your income rather than trying to compound dividends alone.

I too felt like if I am buying monthly dividend-paying stocks, I will be better off. My portfolio would grow faster because I will be getting my dividends more often and thus buying more shares more often and snowballing my dividend income. But I never put the math behind my thinking. And the feeling about the income boost was so good.

But there was something back in my head which was telling me that something was not right, so I sat down to do the math. I hoped to prove myself that by buying monthly payers, my portfolio would grow faster, bigger, and fatter. And I will be rich in 5 years instead of 40 years.

The first thing, which came across my mind was: well, with monthly dividend payers, I get a smaller dividend every month than in three months, I will get the same amount of dividends as in three months. And I will be able to buy the same amount of shares no matter when I get the dividend. At the end of the three month period, I will have the same dividend and same amount of shares no matter if I received the dividend and reinvested it every month or at the end of a quarter.

There is a difference in compounding though. I am not saying that it is all the same. But the difference is so insignificant that it makes no sense to chase monthly payers and put your money in a larger risk.
 
 

I decided to use Gladstone Investment Corporation (GAIN) as an example. GAIN is a widely used darling among dividend investors. I hold a few shares of this stock too, but I am a bit hesitant investing my money into this stock thanks to my past bitter experience with this type of company.

The company was around since 2005 and diligently paid its dividend since then every month. Unlike others, the company never split its stock which is a good thing. It seems, it also never issued an SPO (Secondary Public Offering) which is also a good thing. Splits (reverse splits), SPOs, and dividend cuts are always a sign of value destruction, and if you see your company engaging in this practice, run away. Gladstone seems never engaged in this practice.

The price action of the stock is not very appealing. Right after its inception, the stock got hit hard in 2008-2009 and it dropped from $15 a share to $2.5 a share. From 2011 until 2016 the stock was trading sideways in a multiyear consolidation pattern. It broke up, reached its peak of $15 a share from the pre-2008 crisis, but soon was again hit with the 2018-2019 trade war volatility and in 2020 with the COVID fear. As an investor, you would have to sustain this volatility and rely on dividends only. Unfortunately, the dividends were not any better either. Here is a dividend history since inception:

As you can see, the dividend history is littered with cuts, misses, spikes, lack of growth. If you are a retiree, would you invest hundreds of thousands of dollars in such stock to suffer from price volatility and unstable dividends to live off of them? And if you invested in this stock in 2014 and bought 1000 shares, your initial investment of $8,040 would grow to $9,765 today. A meek 21.46% return over 6 years.

I wanted to see if I compounding the dividend would provide a better result and compared monthly compounding with quarterly. The difference was staggering (well, the lack of any difference).

If I bought 100 shares of GAIN and compounded dividends monthly vs. quarterly for the next 10 years, I would achieve the following results:

It is evident that the difference between the two is so small that it doesn’t justify putting your money into riskier monthly payers. If you feel that the monthly payer will give you better results, then it is just a feeling.
 
 

Many monthly dividend-paying stocks are among REITs, BDCs, or MLPs. And, unfortunately, these stocks are very low quality. There are a few exceptions though. Well, I can only think of one stock exception – Realty Income (O). Everything else out there is garbage, in my opinion.

I used to invest in these stocks but, mostly, I lost money, and dividends received were never able to recover the capital loss, not mentioning providing a sustainable income. And you want income to live off of it not recovering losses.
 

I used to invest in AGNC. Constant dividend cuts and capital depreciation caused my investment to be destroyed. The stock went from $40 a share to $14 a share today. Received dividends never covered the loss.
I used to invest in VNR. The stock went eventually bankrupt and I lost the entire investment. Dividends were not able to cover the loss.
I used to invest in PSEC. The stock fell from $18 a share to $5 a share while the company was constantly cutting dividends. Dividends never covered the loss.
I used to invest in ARR. Another example of value destruction. Constant dividend cuts and reverse split destroyed my value. Dividends were never able to cover the loss.
 

There are many other examples of companies in REITs, BDCs, and MLPs category which would effectively destroy your value. There is no justification to buy these companies when they pay monthly dividends because you may think that they would grow your portfolio faster. They most likely won’t.

The only black sheep (or rather a white sheep) among these stocks is Realty Income (O). It is a company which prides itself to provide value to their shareholders and keep a monthly income coming every month after month. The company even increases its dividend every year (sometimes multiple annual increases). They are proud of it. They know many retirees depend on them, and they strive to not disappoint them. You won’t find many shareholders friendly companies out there such as Realty Income. They even advertise themselves as The Monthly Dividend Company that:

“…started with a simple idea – to use the rent collected from commercial properties held under long-term leases to support monthly dividends to shareholders.”

That, in my opinion, is the only company in the monthly dividend REITs category worth your investment.
 
 

To create monthly income, the only feasible way is to use quarterly dividend payers and stage them so you receive the dividend every month. It takes some effort but you can select stocks in that way that you receive dividends every month. It only takes 12 stocks to create monthly dividend payouts. And, what’s best with this strategy? You can fish among good quality dividend aristocrats. You can choose reliable companies that will grow dividends every year and sustain any recessions without cutting the dividends. Your value will not be destroyed and your income will grow. You will be able to use dividends for your living expenses and not value recovery.
 
 

How can you boost your dividend income then if monthly dividend payers can’t provide it? The only way I know of is to use options. It takes some effort to learn options but if you use a simple strategy of selling covered calls and cash-secured puts to boost your re-investable income, you will not do badly. Your portfolio will grow faster. And what’s best is that you can create a monthly income selling covered calls against your existing quarterly dividend-paying stock.

I traded options in the past a lot. I traded strategies such as Iron Condors, straddles, and strangles. But I traded them for pure speculation. There was no strategy behind the trading. The problem was, I traded just because I had to trade. I had to be in the trade all time and I falsely believed that this would make me rich and my portfolio will grow fast. No, it didn’t. I lost money and I am where I was 6 years ago. I recommend you not going this path. It is a dead-end. It is also a daring admission to finally admit to myself that I was wrong. Or maybe not wrong, just not skilled enough, not educated enough, not a great trading guru as so many on Facebook, who are making millions in a year and never lost a penny (well, maybe only a few pennies).

Since I am not this miraculous financial, CPA, millions making guru from Facebook, I had to adjust my strategy to something more conservative but stable. My goal always was to create income from my investments which can be re-invested to grow my portfolio into a level where the income starts covering my expenses and I can quit my daily job and live off of my dividends and trading. And I had to adjust my mind and my strategy to achieve this goal. And it is working! Finally!

What I decided to do is to accumulate a few good quality dividend stocks and reach 100 shares of each. Then apply a strategy called a “Wheel of fortune“, or a Wheel strategy.

In short, I accumulate shares of my high-quality dividend aristocrats and once I have 100 shares, I start selling covered calls. I try to avoid assignment and have my shares called away should the stock go higher and breach my call strike. In this case, I roll the call higher and usually away in time. I keep receiving dividends and options premiums. If everything goes well, I keep generating income every month, and once every three months I receive two payments (dividends and options premium). Sometimes, I have to roll my options two or three months away to roll higher for credit. And I am OK with that.

If the stock gets called away I start selling cash-secured puts to generate monthly income and eventually buy my stock back and gain 100 shares again. Then I start selling covered calls again.

If I have enough cash in my account to start selling puts before reaching 100 shares of a stock, I start selling puts. Sometimes, I sell the puts without a desire to get assigned and be forced to buy 100 shares of the stock. But in this scenario, I make sure, I do not overdo put selling so if I get assigned I do not suffer huge losses.

I also use this strategy of options selling to replace dividend cuts. In 2020 many great companies decided to cut or suspend dividends. Disney (DIS) suspended its H1 (first half of the year) dividend, Helmerich & Payne (HP) cut the dividend (HP was a dividend aristocrat with 47-year dividend increases), Wells Fargo (WFC) cut the dividend by 80%, Meredith (MDP) cut the dividend after 27 years of dividend increases, Dominion Energy (D) cut the dividend, BP, BA, cut the dividend, and these are only among the good quality stocks that cut their dividends. Many not so good quality companies cut the dividends too. And, unfortunately, we may see more cuts or suspensions coming.

Selling options looks like the only way to replace the lost income. It also lowers your cost basis so you hold the stock cheaper and cheaper every year. At some point in the future, you will hold the stock for free (the dividends and options premium income will return you all your investment) and in that case, it won’t matter to you what the stock is doing out there.

I also use LEAPS instead of a stock. Usually, I use LEAPS against indexes such as SPY or IWM. To buy 100 shares of SPY at a current price of $336.84 a share, an investor will have to come up with $16,836.32 in a margin account or $33,672.08 in a cash account (such as IRA). Purchasing LEAPS call option would cost $3,941 only. A fraction of what you would need if buying 100 shares.

Recently, I have purchased IWM LEAPS and started selling covered calls against the position (a strategy called Poor man’s covered call). It only cost me $2,255.00 to buy the LEAPS call option. After the purchase, I started selling the covered calls and received $265 in credits. That lowered my cost basis to $1,990:

And, I can reinvest the options income to other stocks and keep accumulating and growing my portfolio. It is not a quick-rich scheme. It is not trading the millionaires from Facebook preach. But it provides a steady income and portfolio growth. And since I started using this strategy, I sleep better. I do not have to be glued to the monitor every Friday to see if my options expire or I will lose money. And, what’s most important? I see my accounts growing again.

If you are interested to see what stocks and what options we trade, then join us at MeWe. We no longer participate at Facebook (very little though) but we are active at MeWe.