MSTR provides AI-powered enterprise analytics software and serves as the world's largest Bitcoin treasury company, offering business intelligence solutions while strategically accumulating Bitcoin as its primary reserve asset. Recently it has pulled back from ~$530 all the way down to $250, so lost more than 50% of its value. And yes, maybe it was over-valued, hyped, whatever, but with the recent Trump comments about BTC and bitcoin recovering back towards $90k, a $260 entrypoint would bring us all the way back to values MSTR was trading at BEFORE Trump was president, so effectively taking our entrypoint back 4 months.

MSTR 9 month performance. Credit: finviz

MSTR seems to have at least a bit of support where it is currently trading, the $250 mark, so it could be worthwhile opening a small position which we should feel comfortable doubling down on a couple of times to make money.

With MSTR trading at ~$260, here are a couple of options trading strategies which could make money, including profit/loss calculations. If you don’t know about stock options, have a look here, where I explain how stock options work using a simple analogy anyone can understand. If you’re just getting starte on your investing journey - have a look at my services for beginner investors.

But back to MSTR, first and foremost, the simple covered call strategy:

You can buy 100 shares and sell Jan 2026 (9 months) $200 calls for a net entry of ~$146. Max profit if called away at $200 will be $54, for a return of 54/146=37% over 9 months if MSTR doesn’t go down an additional 20% from where it is today. If it expires below $200, you get to keep the shares at a net entry of $146, while the stock was trading at $255. Statistically this strategy has a 63% probability of any profit, as you can see in the screenshot below:

And if MSTR expires below $200 in Jan 2026, from a $146 net entry, you should be able to sell another ~$50-75 of premium over the next year, lowering your entry, again, by an addiitonal ~$50, or down below $100, or less than half what it is today. So this is a great way to buy MSTR for a 100/255 = 39% discount, although this does require an investment of $14.6k.

For anyone who doesn’t want to drop $15k into MSTR, there are other ways to make money. Another option would be to buy a call spread. With MSTR trading at ~$255, down for $540, it seems perfectly reasonable to guess it could go back up above $270, over the next 2 months. So you can open an Apr $260-270 bull call spread for net $4:

MSTR bull call (vertical) spread strategy

The max loss on this trade is the initial debit, so $400, while the max gain is $600. Statistically, this strategy has a 42% probability of any profit, but its only a $400 investment:

In the case MSTR goes down from its current $255, the adjustment to make even more money with a higher probability of success is very simple: roll the spread lower and wider, for the option to make more money at a lower strike price, so obviously a higher probability. Because the initial investment is only $400, you should feel comfortable doubling down at least 3-4 times. So the roll could be from a 260-270-340 spead for $400 down to a 220-240 spread for $900, down to a 170-200 spread for $1900 (max profit $1100) down to a 150-190 spread for $3000 (max profit of $1000 with MSTR above $190 on expiry). So with MSTR trading at $255, even if it goes down another 15% from where we are today, after the adjustments the strategy still makes 1000/3000 = 33% profit on a $3000 investment (up from an initial investment of $400 for a return of 600/400=50%). So instead of making $600, you end up making almost double that at a much lower strike.

And then 1 last option which is a strategy I like to call a covered synthetic long strategy, and is a combination of the above mentioned 2 strategies:

A synthetic long options strategy is where you sell a put and use the proceeds to buy a call. Its a highly directional strategy, similar to buying the shares, but higher leverage. It has the same problem as buying shares though: if the stock goes up and then down you don’t make any money. I much prefer selling calls on top of my shares, as shown in the first example, because it enables you to make money as time goes by, even if the stock doesn’t go up. Selling a call above the synthetic long strategy has a similar effect: It turns the long call into a vertical spread, and can turn the whole position into a net credit, which decays as time goes by. The strikes you choose for the short put and for the call spread are flexible, depending on how direction you would like to be. Me personally I prefer to be conservative when I open a position, which leaves me a lot of flexibility to adjust if the stock goes against me. So for example, you can buy the same Apr 260-270 call spread discussed above, but sell a June (4 months) $150 put below the spread:

The strategy is a net ~$515 credit, which you will make as long as MSTR stays above $150, or 40% lower than it is today. The max profit though is $1000, plus the $500 initial credit, so $1500 profit on a $500 credit position. The position obviously will obviously require margin to cover the short put, but even if you look at it as a cash secured put, its a 1500/15,000 = 10% return over 4 months, or 30%/year return in the best case. In the worst case, you’re require to purchase 100 shares of MSTR at $150, or 40% lower than they are today. The probability of any profit for this strategy is 53%:

Covered synthetic long outcome probabilities

For a margin account, the margin required on the short MSTR puts is only 50%, as this is a growth stock, but still it makes the strategy twice as profitable, as you can leave the other $10k to cover the put in a HYSA and make an additional 4% on it.

As I mentioned, the strikes can be adjusted depending on your outlook for the future for MSTR, but I prefer to be very (!) conservative in my initial investment, which makes adjusting much easier. It essentially turns my “best” case into my worst case: I would almost rather the stock goes against me at first, so I can double down and make more money, rather than the position to immediately go my way in which case I make my “best” case.

So for the above example of the bull call spread, my “best” case is making $600 against my $400 initial investment. But really, I would rather make $1000 than $600, so I would almost rather to be able to double down a couple of times on my initial investment, in order to make more money on a larger investment, than make less money on a small initial investment.

And those are 3 stock options strategies on MSTR (MicroStrategy) stock which take advantage of the recent ~50% drop in MSTR from ATH, which will make money even if the stock doesn’t go back up to its previous highs any time in the immediate future.

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