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@ Chris Liss
2025-05-20 13:49:50I’ve written about MSTR twice already, https://www.chrisliss.com/p/mstr and https://www.chrisliss.com/p/mstr-part-2, but I want to focus on legendary short seller James Chanos’ current trade wherein he buys bitcoin (via ETF) and shorts MSTR, in essence to “be like Mike” Saylor who sells MSTR shares at the market and uses them to add bitcoin to the company’s balance sheet. After all, if it’s good enough for Saylor, why shouldn’t everyone be doing it — shorting a company whose stock price is more than 2x its bitcoin holdings and using the proceeds to buy the bitcoin itself?
Saylor himself has said selling shares at 2x NAV (net asset value) to buy bitcoin is like selling dollars for two dollars each, and Chanos has apparently decided to get in while the getting (market cap more than 2x net asset value) is good. If the price of bitcoin moons, sending MSTR’s shares up, you are more than hedged in that event, too. At least that’s the theory.
The problem with this bet against MSTR’s mNAV, i.e., you are betting MSTR’s market cap will converge 1:1 toward its NAV in the short and medium term is this trade does not exist in a vacuum. Saylor has described how his ATM’s (at the market) sales of shares are accretive in BTC per share because of this very premium they carry. Yes, we’ll dilute your shares of the company, but because we’re getting you 2x the bitcoin per share, you are getting an ever smaller slice of an ever bigger overall pie, and the pie is growing 2x faster than your slice is reducing. (I https://www.chrisliss.com/p/mstr how this works in my first post.)
But for this accretion to continue, there must be a constant supply of “greater fools” to pony up for the infinitely printable shares which contain only half their value in underlying bitcoin. Yes, those shares will continue to accrete more BTC per share, but only if there are more fools willing to make this trade in the future. So will there be a constant supply of such “fools” to keep fueling MSTR’s mNAV multiple indefinitely?
Yes, there will be in my opinion because you have to look at the trade from the prospective fools’ perspective. Those “fools” are not trading bitcoin for MSTR, they are trading their dollars, selling other equities to raise them maybe, but in the end it’s a dollars for shares trade. They are not selling bitcoin for them.
You might object that those same dollars could buy bitcoin instead, so they are surely trading the opportunity cost of buying bitcoin for them, but if only 5-10 percent of the market (or less) is buying bitcoin itself, the bucket in which which those “fools” reside is the entire non-bitcoin-buying equity market. (And this is not considering the even larger debt market which Saylor has yet to tap in earnest.)
So for those 90-95 percent who do not and are not presently planning to own bitcoin itself, is buying MSTR a fool’s errand, so to speak? Not remotely. If MSTR shares are infinitely printable ATM, they are still less so than the dollar and other fiat currencies. And MSTR shares are backed 2:1 by bitcoin itself, while the fiat currencies are backed by absolutely nothing. So if you hold dollars or euros, trading them for MSTR shares is an errand more sage than foolish.
That’s why this trade (buying BTC and shorting MSTR) is so dangerous. Not only are there many people who won’t buy BTC buying MSTR, there are many funds and other investment entities who are only able to buy MSTR.
Do you want to get BTC at 1:1 with the 5-10 percent or MSTR backed 2:1 with the 90-95 percent. This is a bit like medical tests that have a 95 percent accuracy rate for an asymptomatic disease that only one percent of the population has. If someone tests positive, it’s more likely to be a false one than an indication he has the disease*. The accuracy rate, even at 19:1, is subservient to the size of the respective populations.
At some point this will no longer be the case, but so long as the understanding of bitcoin is not widespread, so long as the dollar is still the unit of account, the “greater fools” buying MSTR are still miles ahead of the greatest fools buying neither, and the stock price and mNAV should only increase.
. . .
One other thought: it’s more work to play defense than offense because the person on offense knows where he’s going, and the defender can only react to him once he moves. Similarly, Saylor by virtue of being the issuer of the shares knows when more will come online while Chanos and other short sellers are borrowing them to sell in reaction to Saylor’s strategy. At any given moment, Saylor can pause anytime, choosing to issue convertible debt or preferred shares with which to buy more bitcoin, and the shorts will not be given advance notice.
If the price runs, and there is no ATM that week because Saylor has stopped on a dime, so to speak, the shorts will be left having to scramble to change directions and buy the shares back to cover. Their momentum might be in the wrong direction, though, and like Allen Iverson breaking ankles with a crossover, Saylor might trigger a massive short squeeze, rocketing the share price ever higher. That’s why he actually welcomes Chanos et al trying this copycat strategy — it becomes the fuel for outsized gains.
For that reason, news that Chanos is shorting MSTR has not shaken my conviction, though there are other more pertinent https://www.chrisliss.com/p/mstr-part-2 with MSTR, of which one should be aware. And as always, do your own due diligence before investing in anything.
* To understand this, consider a population of 100,000, with one percent having a disease. That means 1,000 have it, 99,000 do not. If the test is 95 percent accurate, and everyone is tested, 950 of the 1,000 will test positive (true positives), 50 who have it will test negative (false negatives.) Of the positives, 95 percent of 99,000 (94,050) will test negative (true negatives) and five percent (4,950) will test positive (false positives). That means 4,950 out of 5,900 positives (84%) will be false.