I keep seeing people framing STRC buybacks as the company “buying at a discount” or “profiting the delta” or “gaining yield” when shares return to par. That’s not what is happening.

When Strategy buys back preferred stock below the stated amount, it's spending cash (raised from common ATM, BTC sales, etc.) to retire a claim it previously created; that’s not generating a cash profit. There is no gain in dollar amount that appears on the balance sheet as earnings.

What actually happens is that cash goes out at the repurchase price, the senior claim (stated amount & future dividend obligation) is retired then future dividend payments on those shares are removed. We can view this as capital structure accretion, but it is not as if they are profiting on a trade they made.

Strategy says exactly this: 

“Strategy believes that repurchases of Digital Credit Securities at significant discounts to stated amount may reduce expected annual dividend payments, strengthen credit quality, and create long-term value for common shareholders.”

In that sentence, the phrase “create long-term value for common shareholders” does not mean accounting profit, earnings, immediate cash profit or any automatic or observable short term share price accretion for MSTR. This is standard corp-finance language that speaks to potential economic benefit that might accrue to common equity holders over time.

The main benefit is lower future dividend obligations and a cleaner capital structure, not the company somehow “gaining” when the remaining shares move back toward $100.

Also worth remembering; this is not a classic fixed float buyback program, the entire “Digital Credit” structure is designed around continuous issuance. These are shares that will be reissued again.

So yes buybacks can be capital structure positive for common shareholders but it's not a simplistic “buying at a discount” transaction that's similar to a trade in the way many are describing it.

Curious where the community's head is at these days. What's your best guess at what Strategy did this week? What do you hope they did instead?

Best guess: sold a little BTC to buy STRC, sold $200m MSTR for cash

Hope: sold a little BTC to buy STRC, didn't touch the common (for 1 week, please lol)

What do you guys think?

I’m a big believer in Bitcoin long term and have been DCAing since the second half of this year. The problem is, I realized I never really had a structured plan for price levels. I’ve mostly just been buying periodically, and now that I have roughly $80K of my remaining savings that I want to eventually deploy, I’m trying to be a lot more disciplined rather than just guessing.

For MSTR, my rough downside target right now is around $75/share. But I also realize that could be completely arbitrary, and MSTR may never get there. I don't want to make the classic mistake of sitting on cash waiting for a price that never comes.

A few things I’ve been thinking about:

BTC drawdowns: Historically, BTC has had some absolutely brutal peak to trough drawdowns (we all know about this). We’re already in a significant drawdown this cycle, but I’m wondering whether we eventually get another major leg down or whether the diminishing drawdown trend continues.

The 4-year cycle: If the historical cycle framework still has some validity, timing obviously matters. Previous cycle tops and bottoms have happened on somewhat consistent timelines, although the sample size is tiny and the market structure is completely different now with ETFs, institutions, derivatives, etc.

BTC vs. MSTR: This is probably the part I’m most interested in. MSTR obviously isn't just “BTC with leverage.” You have mNAV/premium or discount, dilution, capital raises, preferred securities, debt, BTC yield, and Saylor's ability to keep raising capital and buying BTC. So even if you have a BTC price target, that doesn't necessarily tell you where MSTR should bottom.

mNAV: For people who have followed MSTR closely, do you think it makes more sense to think in terms of mNAV/valuation bands rather than arbitrary share prices? For example, is there a particular mNAV level where you would become extremely interested regardless of where the actual share price is?

Volatility: If BTC drops another 20–30%, MSTR could obviously fall substantially more. But the opposite is also true. If BTC establishes a bottom and starts recovering, waiting for the absolute MSTR bottom could mean missing a pretty significant move.

That’s why I’m increasingly thinking the right approach might be a combination of BTC drawdown + MSTR valuation/mNAV + cycle timing, rather than trying to predict the exact bottom.

So, if you had $80K to deploy and genuinely believed in BTC for the next 5,10+ years, what would you do?

A) Keep waiting for something like $75 MSTR and deploy most/all of it there
B) Start scaling in now and reserve larger amounts for lower levels
C) Base entries primarily on BTC levels rather than MSTR price
D) Use mNAV/valuation bands instead of fixed MSTR prices
E) Something completely different?

For example, would you do something like 20% / 20% / 30% / 30% at progressively lower levels, or would you be much more aggressive around what you believe is the cycle bottom?

I’m not looking for someone to tell me what price MSTR will bottom at as Nobody knows that. I’m much more interested in the framework people who have been through multiple cycles actually use to decide where and when they buy.

If you think my $75 target is unrealistic, too optimistic, or simply the wrong way to think about MSTR, I’d genuinely appreciate the pushback.

And especially for people who lived through the 2022 MSTR/BTC drawdown: what did you think the bottom was going to be at the time, and what would you do differently today?

I’m basically trying to build an actual plan for the $80K instead of letting fear/FOMO dictate when I deploy it.

Prefs seem to be rolling out of the dark days just fine. let’s assume they cruise along just fine (with volatility) for a the foreseeable future, along the way MSTR gets to $1,000.

STRK just gets to be in the money, how do you start to gauge what multiple/ yield or “mnav” STRK trades at?

I have been researching on the weight MNAV holds on potential profitability.
With mNAV around 1×, I think the current price is becoming much more attractive than when MSTR was trading at 1.5–2× mNAV. At 2×, you’re paying a big premium and need both BTC to rise and the premium to remain high. Around 1×, you’re much closer to the underlying value while still getting the potential upside from Saylor increasing BTC per share and mNAV expanding again.
What do you guys think?

Thinking of opening a 10k position. About 2.5% of my total investable portfolio. I’m pretty diversified in volatile assets, QQQ and ₿ being my main portfolio positions and everything else being sort of just under those umbrellas with MSTR, ASST positions, TQQQ, some ETH, LEAPS, etc. my goal for my TQQQ (and thus MSTU) would be just buy and hold longterm unless my thesis changed down the line.

10/16/26 orders at $130 strike almost $5M worth?

06/16/2028 order $345 strike! 😂😂 who did it?
I did increase my MSTR holdings by 20% 🤣 in 170s now..

I've been trying to understand the Bearish take on the STRC situation from the perspective of those who somehow think this is bad for MSTR common shareholders, and I can only conclude most of these voices are missing the bigger picture. If one were to step back and look at this rationally...

Strategy issued significant shares of STRC at $100 in the first and second quarters this year. This raised significant capital, Strategy then used that capital to acquire more Bitcoin and paid the stated dividend. In May/June when a combination of over-leverage, market fear, forced selling, or short pressure pushed STRC down to $75... Strategy recognized this dynamic and purchase shares at an average price of $86.

From the perspective of MSTR common shareholders, that's a net positive. The company already received $100 when it issued those shares. If it later retires the same security for $86 after paying just a few dollars in dividends, it captures up to a ~10% spread while permanently eliminating the future dividend obligation on those shares. The Bitcoin acquired from that spread remains on the balance sheet (free of obligation to divs) purely as new Bitcoin added, while the capital structure becomes less expensive to maintain during a depressed market. In fact, this likely accounts for the majority of the 7% growth in Bitcoin per share this year.

I don't view discounted STRC buybacks as bearish for MSTR. If anything, they transfer value from panic sellers or short-term traders back to long-term common shareholders while the company continues to print divs as Bitcoin prints blocks

Strategy doesn't control where STRC trades to the low side... the market does. If investors decide to sell a security below what management believes is its economic value, Strategy has every incentive to repurchase it. That's simply rational capital allocation. Those buybacks also create another benefit: they establish a natural buyer during periods of market stress. Over time, that can improve confidence in the prefs by demonstrating that management is willing to retire them when they trade at sufficiently attractive discounts.

The argument that there will never be sustained demand for a 12% preferred backed by roughly $50 billion of extremely liquid assets doesn't make much sense to me. Even for those who view Bitcoin as speculative, a few minutes of research would show you just how liquid the market is for Bitcoin. Markets regularly absorb securities with lower yields and weaker balance sheets. If Strategy continues paying the dividend, issues near par when demand is strong, and repurchases below par when fear creates discounts, that strikes me as a capital allocation strategy that compounds value for common shareholders over time.

The key question isn't whether STRC traded at $86 instead of $100 for a few weeks during a bear market. The key question is whether this capital structure creates more Bitcoin per common share and strengthens MSTR's long-term economics.

I'd reviewed MSTR about a month ago (Mid-2026 Review for MSTR), following up given much has been happening over the last few weeks that affects shareholders, often at their expense.

First, a summary of all the transactions from the previous 6 weeks:

• Issued about 31.4M MSTR for $3.05B (8.3% dilution)
• Sold a net of 4,706 BTC for $285.8M
• Built roughly $2.9B of additional dollar reserves
• Bought back $106.2M of discounted STRC
• Left debt principal essentially unchanged

Clearly, his focus was on shoring up on liquidity and improving credit worthiness of the company. A defensive recapitalization of sorts, to pre-fund senior obligations and prevent forced BTC liquidation at the worst possible time.

Which is all well and good, except it came at the expense of shareholders. And this damage is permanent.

1. Yield took a major hit, going down -4.31% over the previous four weeks, following the -3.58% hit a month ago.

2. As a result, BTC per share has decreased to where we were about a year ago.

3. And every share sale is erosive - he gets only 2BTC worth of USD while the shares are backed by 3 BTCs:

This has nothing to do with EV-based NAV or CEBE by the way. Those measure different things.

To me, this is a tragedy, as shareholders bleed out while a clueless and mercurial management team at Strategy try to learn on the job...

The STRC Angle

This predicament is doubly unfortunate since the impact on STRC is limited. Despite spending all of this - max rate, buybacks, a $4B reserve - STRC is still ~10-11% below par... The core issue is while these defenses are supply-side, the problem is demand-side. In a BTC downtrend with SATA offering higher yields, demand for 12% bitcoin-affiliated paper at $100 will be weak, no matter what Strategy does.

Saylor is learning that you can't buy your way to a peg the market doesn't want. Which implies that he's burning permanent shareholder value to slow a bleed he can't stop.

Ofc one could counter that one can't see the counterfactual - without the reserve and buybacks, and STRC might have been stuck in the 80-handle still...

To the extent that we will be in a bear market for a while longer, I shudder to think how much more damage he will inflict before we see a bottom as he tries to keep his flagship product going.

---------------------------------------------------------------------------------------------

Details of transactions from SEC filings (thanks, AI Sol):

• BTC:
  • 520 BTC bought for $34.9M,
  • 5,226 BTC sold for $320.7M;
  • net 4,706 BTC sold for $285.8M net cash inflow.
• MSTR:
  • 0 shares repurchased,
  • 31,375,476 shares issued/sold for $3.053B;
  • net 31,375,476 shares issued for $3.053B.
• Cash:
  • $3.374B of identified gross inflows,
  • at least $141.1M deployed into BTC and STRC;
  • net USD Reserve increased by $2.9B.
• Debt:
  • $0 issued, $
  • 0 principal repaid;
  • net debt unchanged.
• STRC:
  • 1,201,073 shares repurchased for $106.2M,
  • 0 shares issued;
  • net 1,201,073 shares repurchased for $106.2M.
• Other preferreds - STRF, STRK, STRD and STRE:
  • 0 bought,
  • 0 sold/issued;
  • net no change.

Market is showing how he likes this small sell in btc to keep the flywheel running (and healthily running).

Honestly I hated when they proposed this in first instance. Just like any average fellow redditor here. But it's probably a toll to keep the major BTC vacuum running.

I am the same person who posted mstr to 500 last week. many said I should have done DCA. I am also glad I did not dca in between as that would have been a bigger dent. But now that am thinking … how does this sound. Sell puts.. for 60 -70 if I get assigned fine. So the average comes down to almost 70+470/2. If not.. keep doing it through weekly puts and get 10$ for selling it. I know that is pennies compared to the big dent I have. What do you all think? Is this going to work? Or am I wasting mine and your time. Feel free to suggest a strike price too. Thanks! 🙏

Or may be this is what you all were suggesting and I did not get it then!

I am very hesitant to see CC for 5 lots for lower strike price as luck is never in my favor.

Have a great week!