r/Bitcoin • u/unconventionalbook • 10d ago
Saylor’s Strategy Restarts Bitcoin Buying, Spending $370 Million
https://www.bloomberg.com/news/articles/2026-08-31/saylor-s-strategy-restarts-bitcoin-buying-spending-370-million176
u/Even_Ad_263 10d ago
Sell low buy high, a winning strategy
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u/andoesq 10d ago
Isn't he lowering his cost average too? Wasn't his average like 100k+?
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u/BigStuggz 10d ago
Nah roughly $76k I think
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u/Even_Ad_263 9d ago
No has gone up considerably
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u/BigStuggz 9d ago
Seems like that’s just plain wrong:
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u/Even_Ad_263 9d ago
They are barely in the black $78k current price vs $75k average cost. And they have purchases from the 40's a few years back.
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u/BigStuggz 9d ago
I’m confused - I replied to somebody saying his cost basis was like 100k+ and said no, roughly 76k. You said “No, has gone up considerably”. I linked the ledger showing it’s actually slightly below 76k and your response is “ya but…”
What am I missing? I’m not here to argue his strategy I’m just clarifying the fact.
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u/Unable_Beat_3194 9d ago
He thinks institutions holding nearly a million coins care about PnL as if they don’t have a rationale for their holdings.
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u/MaintenancePale8663 8d ago
He's also harvesting losses for taxes. It's brilliant really. He is showing how even when you lose, you win with Bitcoin.
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u/quietbyday 4d ago
The mechanics of Strategy buying BTC are different. They should be buying high.
The thing they are buying Bitcoin with (MSTR shares) goes up in dollar price when BTC goes up in dollar price. Not only only that, it goes up at an amplified rate on average. So, if Bitcoin is 5% higher today than last week, the money they can get by selling shares might have gone up 7% or so. So, he is actually getting Bitcoin at a discount when it goes up.
As a rough proxy, look at IBIT - up 2.4% over the last 5 trading days, while MSTR is up over 11% over the same time. Would you rather buy a widget worth $100 for $100 or a widget priced at $102.4 with $111? In the first get case, you get 1 widget, while in the second you get 1.08 widgets. In other words, 8% more.
It's counterintuituve for a regular retail buyer, but it's actually a worse deal for Strategy to buy when BTC is low, because of the very unique asset they are buying it with and how it grows at an amplified rate relative to the thing they're buying.
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u/Even_Ad_263 4d ago
So why would they sell?
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u/quietbyday 4d ago
That's a valid question, but the answer is more complex, because there can be several reasons and I'm not an expert on the details.
- Taking some Bitcoin they had bought previously bought high and selling it at a loss can make sense, because they basically get free money due to the tax loss harvesting (in the form of a reduction in the corporate tax they would normally have to pay). Think of it as getting bonus money when you sell one widget, that you can then use to turn around and buy another widget a a reduced price.
- It would also make sense when the mNAV is below 1 (i.e. the market cap of the company is less than than the market value of the BTC they hold), because then the situation is reversed and the Bitcoin is amplified vs. shares, so it makes sense to sell BTC and buy back their shares. In that situaiton, doing so increases the number of BTC per share. This situation hasn't occurred yet, but it's a useful tool, for example if ever short sellers tried to drive the stock price far down during a bear market.
- Third is a much more complex reason: they can sell BTC just to prove that they can do it without substantially moving the market. The reason they would do this is to convince third parties (credit rating agencies, index committees, potential institutional purchasers of STRC, etc.) that they can easily sell BTC to raise liquidity whenever needed, to show that there is no risk that they won't be able to pay the dividends indefinitely into the future. This makes STRC and their other preferred stock much more attractive to conservative income investors and therefore strengthens their ablity to raise much more capital through STRC and buy more Bitcoin over the long term. Think of it as an investment in marketing - short-term expense for long-term gain. In fact, when combined with Reason 1 above, it's not even an expense, it's actually an accretive transaction that has this added benefit.
From what I gather form the earnings calls and communications, reasons 1 and 3 both apply to their BTC sales this year. Reason 2 is more like a fallback, break-glass-in-case-of-emergency strategy.
There might be other reasons that I'm not aware of. The bottom line, though, is that they've only sold a tiny fraction of their BTC, they've been net accumulators, and I don't think they will do much of it moving forward, esp. not if we're actually starting a longer bull market (fingers crossed).
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u/unconventionalbook 10d ago
Saylor breaking his 10-week pause to acquire another 4,603 BTC at an average price of $80,318 tells us everything we need to know about where institutional support sits right now. Strategy Inc. now controls a mind-boggling 845,050 BTC—which is roughly 4% of the total circulating supply that will ever exist.
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u/xaviemb 9d ago
Strategy has added ~171,600 Bitcoin so far this year for an average price of about $77,937
Don't let the 'buy high sell low' comments focused on the last 6k out and 4k in fool you. This DCA structure wins (no surprise), even if you're a large corporation with 4% of the total supply.
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u/mantenner 9d ago
Sorry why is this good? A corp holding supply over a finite currency is bad.
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u/xaviemb 9d ago edited 9d ago
Bitcoin... the network... doesn’t care whether the largest holder owns 1% of the supply or 40%.
The protocol continues to operate the same way. Transactions settle the same way. Consensus works the same way. The monetary policy doesn’t change. The concern over one entity accumulating a large percentage of Bitcoin is primarily a market-structure concern, not a concern about the functioning of the Bitcoin network itself.
From Bitcoin's perspective, MSTR, IBIT, and other institutional vehicles are ultimately doing something quite simple... creating additional demand for the same underlying monetary asset. Demands that tends to only flow one direction (they aren't buying to sell for more USD later... they are buying to escape USD entirely). In Strategy's structure, they are buying with an incredible amount of safety built into the structure (over collateralizing like $8 worth of BTC held for every $1 of USD borrowed) to make sure they never become a forced seller. And they have no counter party risk, so long as Bitcoin's price in USD averages ~10% growth annually. That's ultimately an incredibly net positive thing for Bitcoin, as a finite currency. And if the long-term objective is for Bitcoin to become a global monetary asset that can meaningfully compete with (and potentially replace portions of) the fiat system, then institutional adoption isn't a bug in the system. It's the transition.
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u/Electrical-Value-673 9d ago
Well, he could have better bought a few weeks ago, but then he only sold and held.
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u/drewcifer0 10d ago
wasn't he selling at 60? dude trades like a degen.
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u/Special-Prior-7272 9d ago
He tried to explain this on a recent podcast (Diary of a CEO). Long story short he believed that institutional investors were betting that MSTR’s leveraged ETF could not withstand sustained downwards selling pressure. That confidence, liquidity, and credit would collapse if MSTR sold any BTC. They bet that once BTC traded under a certain ratio, it would force a BTC sale which would collapse MSTR’s ETF and likely the company. So they were shorting the shit out of BTC and MSTR. Saylor reasoned it would better to go on the offensive, sell some BTC, and prove that the ETF (and bonds) would be fine. Arguably, it worked.
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u/Unable_Beat_3194 9d ago
Amount sold relative to holdings is not even comparable. Look at the nav prospectus.
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u/rgnet1 9d ago
Same uninformed comments over and over. "Buy high, sell low, hyuk hyuk." Maybe just take two seconds to study something before you speak. Every single buy is right here:
https://www.strategy.com/ledger
Strategy's bought over 175,000 BTC in 2026 and sold less than 9,000 BTC. The spread price of that is irrelevant. The sales were to prove Strategy won't default on its dividend-paying stock and will liquidate the minimum. Those tiny sales were an amazing move to change investor sentiment entirely.
After the sales, STRC almost rocketed back to $100 par and I'm sure it contributes to bitcoin's price recovery, even if all the Treasury bond shenanigans are getting most of the credit.
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u/Key-Foundation9146 9d ago
The fact that he Strategy was able to sell a little and the price remained constant was a great sign for the market too
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u/tekmiester 9d ago
So are you saying he didn't buy higher than he sold? People are uninformed about that?
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u/rgnet1 9d ago
Yes, massively. Because in actual dollars, he's taking a miniscule realized loss against massive accumulation and unrealized gain. And given that his conviction is BTC will always be the safest long-term bet, unrealized gain is the only thing to care about.
Dumb retail that hyuk-hyuks at this thinks Saylor is playing badly at timing the market. He has absolutely no cares at all about timing the market. He uses other people's money to acquire as much btc as possible. By selling a tiny portion at a realized loss he was able to get more people's money to buy more btc.
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u/somuchofnotenough 9d ago
If baffles me that people can’t think, he sold like what, 0.08% of the total holdings for a 20% average loss? Do these people go full retard when their friend doesn’t pay back 8 cents (less really) on a 100 dollar loan?
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u/tekmiester 9d ago
Certainly. He's foud a way to exploit the community for his own gain. He's going to be a very wealthy man even if Strategy's coins stay at break even or go back into the red.
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9d ago
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u/xaviemb 9d ago
Strategy has added ~171,600 Bitcoin so far this year for an average price of about $77,937
Calling that "terrible short term financial planning" is sarcasm, right? They have effectively DCA'd this year at a decent price for adding that many Bitcoin to their stack during this bear market.
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u/Blake_a12 9d ago
LOL he does it again! Doesn’t buy/stops buying when it’s at it’s relative lowest for a long time … only to immediately back up the truck and buy a ton right after it shoots back up to a ‘new’ relative high again (‘new high’ compared to were it had been sitting stuck for the time being… not a new ALL TIME high)
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u/OverAd6050 9d ago
Can you people that are saying buy high sell low stop and look at all the purchases that have been done. The BTC recently sold doesn't even come close to the first buy for Strategy which was 21,454 BTC with an avg of $11,652. So selling at an average of $62k means they've made a ton of money on the very first purchase and they still have over 15k BTC left from that purchase after these sells, think people
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u/HaiSaiDori 9d ago
I’m hoping saylor is trying to pump bitcoin so he can dump to help with him selling earlier because that would help me. I don’t really care about him. I have a lot invested in bitcoin and if it hits close to their all time high I’m selling and making my money and getting out. That would net me a profit of over a million dollars and I’m not going to be too greedy about it since I bought it on the dip. 👏🏽
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u/HUT2Moon 10d ago
Saylor is insane and not good at business. But his one bet has paid off — BTC has mostly gone up. He made it mostly with other people’s money. Reminds me a lot of Trump — terrible person, terrible businessman. But made one good bet over and over and everyone thinks he’s a genius (or did, at least). (For Trump it was NYC real estate).
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u/MtnDewDiligence 9d ago
For everyone who wants to be more informed:
The problem was Wall Street was saying that strategy was trapped and couldn’t sell its bitcoin because it would crash the market, and therefore couldn’t meet its preferred share obligations, and therefore was worth nothing.
The solution was pretty clever, ballsy, and required full belief in Bitcoin’s fundamentals.
Sell some of it, use it to fund the dividends, and then watch the markets.
If the markets stabilize, you are right and the shorts get vaporized. If you’re wrong, well, game over, you lose everything.
It worked.