@ Chris Liss

I https://www.chrisliss.com/p/mstr a few months ago with the subtitle “The Only Stock,” and I’m starting to regret it. Now, it was trading at 396 on January 20 when I posted it and 404 now (even if it dipped 40 percent to 230 or so in between), but that’s not why I regret it. I pointed out it was not investable unless you’re willing to stomach large drawdowns, and anyone who bought then could exit with a small profit now had they not panic-sold along the way.

The reason I regret it is I don’t want to make public stock predictions because it adds stress to my life. I have not sold any of my shares yet, but something I’ve noticed recently has got me thinking about it, and stock tips are like a game of telephone wherein whoever is last in the chain might find out the wrong information and too late. And while every adult has agency and is responsible for his own financial decisions, I don’t want my readers losing money on account of anything I write.

My base case is still that MSTR becomes a trillion-dollar company, destroys the performance of the S&P, the Mag-7 and virtually any other equity portfolio most people would assemble. Michael Saylor is trading an infinitely-printable asset (his shares) for humanity’s best-ever, finite-supply digital gold, and that trade should be profitable for him and his shareholders in perpetuity.

I don’t know exactly what he plans to do when that trade is no longer available to him — either because no one takes fiat currency for bitcoin anymore or because his mNAV (market-cap-to-bitcoin-holding ratio) goes below one — but that’s not my main concern, either. At that point he’ll have so much bitcoin, he’ll probably become the world’s first and largest bitcoin bank and profit by making his pristine collateral available to individuals and institutions. Even at five percent interest, half a trillion in bitcoin would yield $25B in profits every year. Even at a modest 10x valuation, the stock would more than double from here.

I am also not overly concerned with Saylor’s present amount of convertible debt which is at low or zero rates and is only https://www.strategy.com/. He’s been conservative on that front and only issuing on favorable terms. I don’t doubt Saylor’s prescience, intelligence or business sense one bit.

What got me thinking were some Twitter posts by a former Salomon Brothers trader/prophet Josh Mandell https://x.com/JoshMandell6/status/1921597739458339193 recently. In November when bitcoin was mooning after the election, he predicted that on March 14th it would close at $84,000, and if it did it would then go on an epic run up to $444,000 this cycle.

A lot of people make predictions, a few of them come true, but rarely do they come true on the dot (it closed at exactly $84K according to some exchanges) and on such a specific timeframe. Now, maybe he just got lucky, or maybe he is a skilled trader who made one good prediction, but the reason he gave for his prediction, insofar as he gave one, was not some technical chart or quantitative analysis, but a memory he had from 30 years ago that got into his mind that he couldn’t shake. He didn’t get much more specific than that, other than that he was tuned into something that if he explained fully would make too many people think he had gone insane. And then the prediction came true on the dot months later.

Now I believe in the paranormal more than the average person. I do not think things are random, and insofar as they appear that way it’s only because we have incomplete information — even a coin toss is predictable if you knew the exact force and spin that was put on the coin. I think for whatever reason, this guy is plugged into something, and while I would never invest a substantial amount of money on that belief — not only are earnestly-made prophecies often delusions or even if correct wrongly interpreted — that he sold makes me think.

He gave more substantive reasons for selling than prophecy, by the way — he seems to think Saylor’s perpetual issuance of shares ATM (at the market) to buy more bitcoin is putting too much downward pressure on the stock. Obviously, selling shares — even if to buy the world’s most pristine collateral at a 2x-plus mNAV — reduces the short-term appreciation of those shares.

His thesis seems to be that Saylor is doing this even if he would be better off letting the price appreciate more, attracting more investors, squeezing more shorts, etc because he needs to improve his credit rating to tap into the convertible debt market to the extent he has promised ($42 billion more over the next few years) at favorable terms. But in doing this, he is souring common stock investors because they are not seeing the near-term appreciation they should on their holdings.

Now this is a trivial concern if over the long haul MSTR does what it has the last couple years which is to outperform by a wide margin not only every large cap stock and the S&P but bitcoin itself. And the bigger his stack of bitcoin, the more his stock should appreciate as bitcoin goes up. But markets do not operate linearly and rationally. Should he sour prospective buyers to a great enough extent, should he attract shorts (and supply them with available shares to borrow) to a great enough extent, perhaps there might be an mNAV-crushing cascade that drives people into other bitcoin treasury companies, ETFs or bitcoin itself.

Now Saylor as first mover and by far the largest publicly-traded treasury company has a significant advantage. Institutions are far less likely to invest in size in smaller treasury companies with shorter track records, and many of them are not allowed to invest in ETFs or bitcoin at all. And even if a lot of money did go into any of those vehicles, it would only drive the value of his assets up and hence his stock price, no matter the mNAV. But Josh Mandell sold his shares prior to a weekend where bitcoin went from 102K to 104K, the US announced a deal with China, the mag-7 had a big spike (AAPL was up 6.3 percent) and then MSTR’s stock went down from 416 to 404. As I said, he is on to something.

So what’s the real long-term risk? I don’t know. Maybe there’s something about the nature of bitcoin that long-term is not really amenable to third-party custody and administration. It’s a bearer asset (“not your keys, not your coins”), and introducing counterparty risk is antithetical to its core purpose, the separation of money and state, or in this case money and bank.

With the bitcoin network you can literally “be your own bank.” To transact in digital dollars you need a bank account — or at least a stable coin one mediated by a centralized entity like Tether. You can’t hold digital dollars in your mind via some memorized seed words like you can bitcoin, accessible anywhere in the world, the ledger of which is maintained by tens of thousands of individually-run nodes. This property which democratizes value storage in the way gold did, except now you can wield your purchasing power globally, might be so antithetical to communal storage via corporation or bank that doing so is doomed to catastrophe.

We’ve already seen this happen with exchanges via FTX and Mt. Gox. Counterparty risk is one of the problems bitcoin was created to solve, so moving that risk from a fractionally reserved international banking system to corporate balance sheets still very much a part of that system is probably not the seismic advancement integral to the technology’s promise.

But this is more of a philosophical concern rather than a concrete one. To get more specific, it’s easy to imagine Coinbase, if indeed that’s where MSTR custodies its coins, gets hacked or https://www.chrisliss.com/p/soft-landing, i.e., seized by an increasingly desperate and insolvent government. Or maybe Coinbase simply doesn’t have the coins it purports like FTX, or a rogue band of employees, working on behalf of some powerful faction for “https://www.chrisliss.com/national-security-and-public-healt” executes the rug pull. Even if you deem these scenarios unlikely, they are not unfathomable.

Beyond outright counterparty malfeasance, there are other risks — what if owning common stock in an enterprise that simply holds bitcoin falls out of favor? Imagine if some new individual custody solution emerges wherein you have direct access to the coins themselves in an “even a boomer can do this” kind of way wherein there’s no compelling reason to own common stock with its junior claims to the capital stack in the event of insolvency? Why stand in line behind debt holders and preferred shares when you can invest in something that’s directly withdrawable and accessible if world events spike volatility to a systemic breaking point?

Things need not even get that rocky for this to be a concern — just the perception that they might could spook people into realizing common stock of a corporate balance sheet might be less than ideal as your custody solution.

Moreover, Saylor himself presents some risk. He could be compromised or blackmailed, he could lose his cool or get into an accident. These are low-probability scenarios, but also not unfathomable as any single point of failure is a target, especially for those factions who stand to lose unimaginable wealth and power should his speculative attack on the system succeed at scale.

Finally, even if Saylor remains free to operate as he sees fit, there is what I’d call the Icarus risk — he might be too ambitious, too hell-bent on acquiring bitcoin at all costs, too much of a maniac in service of his vision. Remember, he initially bought bitcoin during the covid crash and concomitant massive money print upon his prescient realization that businesses providing goods and services couldn’t possibly keep pace with inflation over the long haul. He was merely playing defense to preserve his capital, and now, despite his sizable lead and secured position is still throwing forward passes in the fourth quarter rather than running out the clock and securing the W.

Saylor is now arguably less a bitcoin maximalist and advocate, articulately making the case for superior money and individual sovereignty, but a corporate titan hell-bent on world domination via apex-predator-status balance sheet. When is enough enough? Many of the greatest conquerors in history pushed their empires too far until they fractured. In fact, 25 years ago MSTR was a big winner before the dot-com crash during which its stock price and most of Saylor’s fortune were wiped out when he was sued by the SEC for accounting fraud (he subsequently settled).

Now it’s possible, he learned from that experience, got up off the mat and figured out how to avoid his youthful mistakes. But it’s also possible his character is such that he will repeat it again, only this time at scale.

But as I said, my base case is MSTR is a trillion-dollar market cap, and the stock runs in parallel with bitcoin’s ascendance over the next decade. Saylor has been https://www.strategy.com/, prescient, bold and responsible so far over this iteration. I view Mandell’s concerns as valid, but similar to Wall St’s ones about AMZN’s Jeff Bezos who relentlessly ignored their insistence on profitability for a decade as he plowed every dollar into building out productive capacity and turned the company into the $2T world-dominating retail giant it is now.

Again, I haven’t (yet) sold any of my shares or even call options. But because I posted about this in January I felt I should at least follow-up with a more detailed rundown of what I take to be the risks. As always, do your own due diligence with any prospective investment.