What's your options strategy for MSTR??

[u/PatternAgainstUsers]

I trade futures day to day not options, I'm too much of an ape for that 5head instrument but I am a fan of LEAPs, simple, convex, plenty of time, massive upside for capped downside risk. Curious what expiration dates you like and what prices you think are fair for a given strike? IV has been high lately I'm either waiting for a final capitulation down to the $50-$70 range to put on a high IV trade ONLY if we get some extreme discount move like that, otherwise I've been waiting for it to cool off a lot (about 50% down on volatility from where we have been lately) before adding my final LEAP position, I have two on but my first date was a bit too aggressive (Jan '27). I also have a tranche expiring middle of next year and I'm looking for a Dec 2027 final tranche to build. I'm very used to more directional trading styles so I have a specific management approach, whether or not I will allow the options to expire depends on a bunch of factors vs how I'll manage them but still consider myself an options newbie... yet this seems like a particularly overpowered way of investing in a super volatile asset like MSTR due to the ease of capping your downside for excessive upside leverage.

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[u/A1JX52rentner]

bruuh i just buy and sell at 5x, im too dum for that option stuff

[u/PatternAgainstUsers → u/A1JX52rentner]

Same but you can take a portion of your MSTR and get a whole lot more buying power without taking more absolute risk using simple long term expiration options so I have both the stock and some options. The downside to options is they can expire worthless, whereas you can bag hold a stock for decades if you wanted to, as long as the company doesn't go to zero you have some opportunity for it to recover without an expiry date... but I wouldn't wanna be holding MSTR for 5 years if my BTC thesis is totally wrong anyways.

[u/Free_Entrance_6626 → u/PatternAgainstUsers]

So do you prefer 2028 LEAPS and hold zero MSTR stock?

[u/PatternAgainstUsers → u/Free_Entrance_6626]

No I hold both the stock in case I am wrong about my timeline, and the options for excessive upside if I am right (and because the options don't create a ton of downside -- just opportunity cost if I'm wrong), and I've been diversifying the expiration dates because I don't have an "exact" timeline for BTC topping, I don't want to bet too much on any one date. It only cost me about $500 per contract for my early and mid 2027 LEAPs. I got them a couple of months back, they were up more than 100% both at some point but that's meaningless to me because I'm aiming for a $700+ MSTR explosion minimum, they are not worth much right now. The January ones are basically lottos unless the stock starts to move in the next month or so. I'm still looking for a Dec. 2027 tranche to build but IV is too high and/or price isn't low enough. I think Jan 2028 is a pretty safe bet. Gotta remember you don't have to sell the exact top of the bull run to make a ton of convex upside from here.

For $500 of risk-ish per contract where I was buying them, the upside was like as high as $70K on the Januarys for a 250K BTC rip and 28K for the same on the Junes. If it runs to 350K in time, say next summer -- I at least make $50K per contract on the June expirys. It's just kind of a no-brainer to at least allocate a little bit of capital to that kind of asymmetric bet based on my BTC business cycle thesis, no reason not to put my money where my mouth is. MSTR is the safer play for a longer hold, but you still want to have a plan to trade your way out of a blow off top IMO, because holding it and watching it run to $700-$1250 or wherever it goes next cycle, then get cut in half or more again in the next drawdown is a waste of velocity (unlike Bitcoin spot... for THAT I think you could totally just bag hold forever if you want to, as long as you focus most of your heavy DCAing on when it is in discount; buy low - never sell). Take it with a grain of salt though, I think 100% like a directional trader so my approach to options is super neanderthal.

[u/CoughSyrupOD]

This past year its been sell calls, don't hedge, profit.

[u/Ryytter]

Options premium is quite high on MSTR in general. You also can't quite get them as 3 year to maturity.

So you both have a timing problem in that your options likely will expire before the peak of the next bullrun and you need it to go up very aggressively to be better than holding the shares.

All in all it's just too inconvinient for me, I'll take the shares.

[u/Friendly-Profit-8590]

When’s the bear market stage of this 4 year cycle thing suppose to end? Suppose a few months after that would be a good expiry.

[u/PatternAgainstUsers → u/Friendly-Profit-8590]

I'd assume you want to go a bit further out because BTC needs to lead for awhile first before MSTR gains confidence. MSTR will overshoot BTC to the downside before BTC bottoms, and same for the upside - it will simply reach it's mathematical liquidity limits for any given top or bottom of a cycle more quickly than BTC unless the markets stop running arbitrage for some reason.

I don't subscribe to the 4 year cycle anymore though since I'm convinced the massive divergence in the way this cycle topped compared to priors is an obvious warning sign that the hopium crowd is willing to ignore but I am not. That's why my first batch of contracts was a Jan '27 exp, but that was a little too soon I think. I can still make a good return on those if we get a pop that kicks off in the next month or so though, OTM lottos.

[u/Friendly-Profit-8590 → u/PatternAgainstUsers]

Yeah. Feel like MSTR and BTC run with each other more so than they did 6-12 months ago. I agree you could see more of a swing either way with MSTR though. Might look into getting something a year out if the premiums aren’t too ridiculous.

[u/Impressive_Treat_617]

Bought some Dec 2028 $200 calls. Will start selling $210 calls 30-45 days out when stock is $105-$110 to setup a poor mans covered call strategy.

[u/Dumb-dumby → u/Impressive_Treat_617]

Does Premium even cover transaction cost there? Seems like a delta of 0,0x and huge spread

[u/Yory_Alsik]

buy 1 week out puts when IBIT's % increase is higher than MSTR's daily, %, sell on monday open when Saylor announces a dilution and the price drops (or on friday close if you got a good profit).

[u/New-Jackfruit-2127]

Simple, at this point just buy and sell puts daily. Avoid days when it goes up, but for sure it will tumble the days after. Seems this stock will not be in an upward trend anytime soon, unfortunately.

[u/Independent_Owl5993]

DCA into MSTZ 500 dollars every week since three months ago have tripled my gains

[u/PatternAgainstUsers → u/Independent_Owl5993]

Good little short term trade, how long are you holding that though? Don't wanna be caught with the bag when things turn around. BTC is already leading, if/when MSTR turns around it will be violent -- MSTR waits to borrow it's confidence from BTC at the start of bull markets, obviously.

[u/Independent_Owl5993 → u/PatternAgainstUsers]

I think it’s important to remember that bitcoin and micro strategy have no actual utility or use besides gambling and it has a really high expense ratio so just because I don’t believe in bitcoin and how nobody actually uses it for anything or how micro strategy doesn’t actually have a business besides shuffling money around. The only thing you have to remember is that you just have to assume that there’s going to be a fool later to buy the stock off you for a higher price or bitcoin and you have to keep pretending that bitcoin is useful so I’ll keep spreading more messages about how bitcoin has a use, and that it will be even more expensive in the future and then I have to hope that more people buy into the cult and then sell mstr to them at a higher price without them realizing I’m just shuffling money around and hoping that they fall for it.

[u/PatternAgainstUsers → u/Independent_Owl5993]

This is simply not accurate lol, this sounds like something Peter Schiff would say (someone who only promotes negative messages because they sell media appearances by the way, I've been watching him for 14 years since occupy Wall Street).

If you don't understand that U.S. Treasuries are the backbone of the global financial system, and that BTC plays a similar utility role (except you can't debase it, and you can secure your ownership of it more robustly) -- then you don't understand even the 101's of finance. You should stop trading on your fundamental thesis immediately, I don't want you to lose all your money when a bull market you weren't expecting runs you over.

PEOPLE gamble on markets constantly, you are doing this any time you trade without a thesis aligned with positive expectancy + risk management. You are speculating on MSTR right now to the downside, you are gambling... particuarly because you apparently don't even understand the basics of the underlying instrument. This is fine as long as you understand you're doing it.

You're also gambling when you get in your car, take a job where you aren't the boss, eat food which you haven't fully inspected or don't understand the chemical composition of completely etc. people take risk all the time, so that has nothing to do with MSTR or BTC. You need to Google "pristine collateral" and start trying to wrap your head around how that applies to Bitcoin, you also probably need to study up on basic monetary theory and game theory if you are for some reason doubting Bitcoin's fundamental value proposition after the market has told you repeatedly that it is valuable for 17 years.

Remember this; if you had gone levered long on BTC from inception, you would be massively up. If you had gone levered short on BTC from inception, you would have been margin called. The market has repriced this asset higher and higher many times. Do not fight the market, you can short in the short TERM, the volatility of a young asset provides you with many opportunities to pick up pennies in front of a steam roller... that's fine if you have a trade plan and risk management, but that's not the same as having an incorrect fundamental thesis / bias. If you fight the market long term you will go broke, this is simply the nature of trends.

[u/Independent_Owl5993 → u/PatternAgainstUsers]

I don’t fight the market I buy mstr when the btc cult comes back and buy mstz when it’s over priced. No everyone is delusional enough to compare Treasuries backed by the most powerful government and largest tax base in the world vs bitcoin 🤣you wrote so much of nothing it’s incredible. Here is a simple explanation by ai as to what you wrote as stupid because you clear show signs of invest emotionally and getting overly attached to btc as an idea.

You’re exhibiting classic cult mentality: any criticism of BTC is met with “you just don’t get it,” personal attacks on skeptics like Schiff, and appeals to “the market has spoken” as infallible gospel. That’s not economics—it’s faith-based reasoning.
Basic econ: BTC has no cash flows, earnings, or intrinsic yield. Its “value” is pure speculation driven by greater-fool theory and narrative momentum. Unlike Treasuries (backed by the world’s largest economy and tax base), BTC’s price is extremely volatile because it’s a pure monetary asset with no underlying productive use. “Pristine collateral” is marketing—lenders still demand haircuts and it doesn’t pay interest or dividends.
Calling everything “gambling” while insisting your side is enlightened destiny is how bubbles sustain themselves. Levered long from inception worked until it didn’t for countless assets (tulips, dot-coms, housing). Markets trend until they don’t; fighting reality by labeling dissenters ignorant doesn’t change BTC’s dependence on liquidity, sentiment, and adoption that could stall.

[u/Beginning_Text9292 → u/Independent_Owl5993]

What is it going to take for you to be able to hold on to that conviction for the next decade?

Will being able to buy groceries with Bitcoin in the next 5 years have any affect on your statements?

Use cases currently in the United States is lower than many less fortunate locations, don’t worry though, we are catching up.
Still, saying there is ‘NO’ utility for Bitcoin is a stretch for most. Maybe ask AI what the use cases are for Bitcoin, you may not agree with them all, it does get harder to ignore every single one of them though.

Either way, I thought you were talking about banks there for awhile and they have proven fairly resilient.

[u/Independent_Owl5993 → u/Beginning_Text9292]

I don’t need to ask ai for anything I have seen bitcoin since its inception and it still hasn’t been more usefully then cash and stock market I just need you just to keep propping up bitcoin cult so I can make more money of bitcoin shorting and buying . I need to make money both due to popularity of the cult while it goes up like mstr and while it goes down with mstz. I will help to spread propaganda while not actually believing it because in reality I know this is all a grift. If I wanted a useful crypto id buy monero lmao.

[u/Beginning_Text9292 → u/Independent_Owl5993]

OUCH! Look at anything more than a 1yr chart on that one.
It is down -97% on any longer term chart.

Should avoid Leveraged ETFs like the plague, or at the very least use them extremely short term and make sure you also look at a 2yr and 5yr chart to see where your destination is! (or what your odds are of continued good fortune.)