Had you glanced too quickly at the crowd packed into Michael Saylor’s Tuscan-style Miami compound, you might have assumed it was just another rich dude’s party. There was all-you-can-eat jamón Ibérico, an ample Versailles-style ballroom where a D.J. spun electronic music and a row of friendly attendants collecting shoes at the entryway to a docked yacht, one of at least three that Mr. Saylor owns.
Matters got considerably weirder at dinnertime, however, when fluorescent green lasers shot out of the host’s eyeballs, or so it appeared to hundreds of guests seated around giant screens erected on the billionaire’s lawn on New Year’s Eve 2024.
The screens plopped Mr. Saylor’s visage into famous films, such as “Gladiator” and “The Lord of the Rings.” He was edited into the action as a hero whose eyes blasted wealthy cryptocurrency skeptics including Bill Gates and Jamie Dimon, the bank executive.
“Buy!” cried Mr. Saylor’s avatar, as opponents were vaporized.
Bitcoin has attracted plenty of prophets, braggarts and flat-out baddies. Of late, though, no one in the industry is attracting more attention and scorn than Mr. Saylor, a would-be magnate and accused tax scofflaw who in six short years has transformed his also-ran technology company, Strategy, into a Bitcoin betting machine.
Strategy’s longtime business is selling corporate software to sort sales data into easier-to-view reports. This is now more or less beside the point: Mr. Saylor has woven a web of financial tools and borrowing agreements to funnel nearly all of Strategy’s available funds into cryptocurrency, a volatile, lightly regulated space that has nothing to do with the company’s traditional business.
That was, on its own, remarkably bold or stupid, depending on who is asked. It certainly worked uproariously for a spell; once a penny stock, Strategy soared to $474 a share last summer as crypto rallied and the company amassed more Bitcoin, as a share of the total world supply, than the U.S. government’s stockpile of gold at Fort Knox.
Mr. Saylor, 60 years old, was estimated to be worth more than $10 billion on paper and given nicknames like Captain of the Digital Navy and, more simply, the Messiah. On social media, he fueled the fire with incessant, outlandish posts that foretold doom for the U.S. dollar and advised the public never to give up on crypto. (“Sell a kidney if you must, but keep the Bitcoin,” he wrote on X.) Eric Trump feted him at Mar-a-Lago.
And yet that proved to be just the start. Over the past year, Strategy rapidly created and marketed a suite of investment products that purport to transform Bitcoin, a notoriously jagged asset, into a safe investment for the masses.
Mr. Saylor crisscrossed the world by private jet, using high-minded financialese to promise fixed returns into the double digits to investors who buy certain types of the company’s shares. He compares its safety to a bank account.
Except, of course, it’s a bank account that takes your money and puts it all into crypto.
How Mr. Saylor, Strategy’s executive chairman and owner of nearly half its controlling shares, is able to justify his promises is complicated. And it’s getting more so by the minute because his company’s project continues to evolve in the face of the latest crypto downturn.
The man who told everyone else never to sell Bitcoin has recently hinted that his company may do just that to meet loan obligations. Strategy has begun to borrow money not to buy more crypto but to stash billions in U.S. dollars — roughly the equivalent of Heinz’s saying it is beginning to see the merits in Hunt’s ketchup.
To skeptics — and there are plenty, even among crypto enthusiasts — it was only the latest sign that Mr. Saylor is a plain old huckster on the edge of unraveling for all to see.
Strategy’s stock now trades at two-thirds below its peak, a far steeper slide than Bitcoin. The crypto community is increasingly on edge that if Strategy, its biggest whale, begins selling, the market at large could tip. That would reverberate to more mainstream financial firms like Fidelity, Barclays and Cantor Fitzgerald, which do business with Strategy, to say nothing of the scores of ordinary investors who bought into Mr. Saylor’s steady sales pitch.
And it would certainly not bode well for dozens of other companies that followed his lead to load up on crypto — among them Trump Media & Technology Group.
The noted short-seller Marc Cohodes predicts that Strategy will inevitably collapse and dismisses Mr. Saylor as a “preacher and a Jim Jones-type.”
“We’ve stayed away,” said Jan van Eck, founder of the namesake investment giant and a crypto investor himself. “It’s just publicity.”
Herb Greenberg, a veteran financial analyst, calls Strategy a “quasi Ponzi scheme” in which current investors can be paid back only with money from new investors.
Mr. Saylor and representatives for Strategy declined to comment for this article.
Asked by CNBC a year ago to address the Ponzi chatter, Mr. Saylor responded: “Just like developers in Manhattan, every time real estate goes up in value they issue more debt to develop more real estate. That’s why your buildings are so tall in New York City. It’s been going on for 350 years. I would call it an economy.”
The Frustrated Fighter Pilot
For much of crypto’s history, Mr. Saylor and Strategy weren’t in the picture.
The suburban Virginia company, originally called MicroStrategy, made its name before the 2000s dot-com boom as a vanilla data-crunching firm that helped companies such as McDonald’s analyze customer information. It had modest revenue and profits, but its stock became a darling as Mr. Saylor emerged as an omnipresent media figure. He had a colorful back story — a heart murmur reportedly prevented him from becoming a fighter pilot — and a penchant for wild, often unrealized promises.
For Forbes in 1998, the year MicroStrategy became publicly traded, he predicted a day when “everybody on the planet lives every hour of every day dependent upon our technology.” To one employee, he mused of developing brain implants.
As Washington City Paper put it in 2000, “Saylor is apparently programmed to never shut up.”
That year, the Securities and Exchange Commission rolled in with fraud charges, saying the company had jiggered its accounting to create the illusion of profits that never existed. Mr. Saylor and his partners agreed to pay millions of dollars in personal penalties but neither admitted nor denied fraud. The company’s shares cratered. Mr. Saylor laid off staff but built the company back to profitability as a midsize software vendor.
Still wealthy, Mr. Saylor retreated to rich-person hobbies. He ran an internet college, Saylor Academy, and combined three Georgetown apartments into one. One of his yachts made an appearance in the “Entourage” movie.
He never lost his taste for experimentation; MicroStrategy designed software for iPads and built a business around scraping social media data. He also hoarded internet domain names, including michael.com and mike.com, both of which he still controls.
But by 2014, Mr. Saylor and the company was again attracting negative attention. This time it was from an unhappy hedge fund investor who described Mr. Saylor as distracted by partying. The fund asserted to the company’s board that Mr. Saylor had driven MicroStrategy into a “pariah status on Wall Street,” and pointed out that the company held more than $350 million in cash that could be invested for higher returns.
Flanked by lawyers, Mr. Saylor met with a group of investors and promised to spend more time on the business, according to a person present, who asked not to be identified because it was a private meeting.
Mr. Saylor also pledged to find a use for the company’s cash.
‘An Escape From Economic Slavery’
He hadn’t done much on that front by the time Covid-19 arrived. MicroStrategy still had half a billion dollars to spend as Mr. Saylor retreated to Miami and began discursive poolside discussions with a neighbor and early crypto evangelist, Eric Weiss, the two men have recounted in podcast interviews.
Years earlier, Mr. Saylor had tweeted that Bitcoin’s days were numbered. Over a week or so of chats, he changed his mind. He became convinced that the Federal Reserve’s pandemic response, including slashing interest rates and increasing the supply of dollars, would debase the U.S. currency and give rise to digital alternatives. He was further hardened in that view by a lack of trust in existing governmental institutions — a common crypto tenet.
Mr. Weiss suggested a small personal investment in Bitcoin, according to the interviews both men have given. Mr. Saylor surprised him in June 2020 with a phone call to announce that he had personally bought $100 million worth, while Bitcoin was trading around $10,000.
MicroStrategy quickly followed. That August, the company announced that it would spend the vast majority of its cash to acquire Bitcoin and to buy out shareholders who didn’t agree.
Mr. Saylor publicly characterized the move as “an escape from economic slavery.”
Also relevant: MicroStrategy’s main software business was struggling to sign up new clients amid the pandemic, with revenue at the lowest level in two decades.
There is nothing necessarily unusual about a company’s using its balance sheet to fund outside endeavors. Insurance companies operate vast investment arms to profit off premiums before they have to pay out claims, while big retailers often buy real estate.
But this shift was extreme. MicroStrategy began doing just about anything to acquire crypto. It regularly issued new shares to the public and borrowed money at low interest rates. Any funds from either were swiftly invested in Bitcoin.
It had acquired $1.9 billion of Bitcoin by March 2021, $2.9 billion one year later and $23.9 billion at the end of 2024, according to filings.
Mr. Saylor’s vocabulary changed, too. He began to publicly describe Strategy (the new name was officially imposed last year) as a “Bitcoin treasury company.” That’s a fancy way of saying its purpose was to wholly invest in crypto.
One might reasonably wonder what the point to all that was; anyone who wants to buy Bitcoin, after all, can easily do that directly.
The answer is twofold. First, partly because of Strategy’s enthusiastic use of leverage, the company’s stock swung higher than Bitcoin when the crypto was up: For each $100 sold of Strategy shares, the company can buy more than $100 worth of Bitcoin because it has borrowed extra money, or issued debt, for that purpose.
And the type of debt in play is important. Much of Strategy’s borrowing has been through “convertible” bonds in which investors accept shares — rather than money — when the loan comes due.
Ordinarily, such loans carry interest like any other. But Strategy stock was for years on such a tear that some investors were willing to lend at a nearly unprecedented zero percent rate in exchange for a future promise of what would become more valuable shares.
Thus, Strategy was able to raise money for free. And it used that money to, you guessed it, buy more Bitcoin.
Call it a loop, a flywheel or an infinite money glitch — all terms that financial professionals use to describe it.
Or call it a disaster waiting to happen.
An Economic Curiosity
What changed for Mr. Saylor and Strategy over the past year isn’t just that Bitcoin’s price slid. It’s that Mr. Saylor began aiming for a broader market of investors that he called the “Bitcoin-curious.”
In early 2025, Strategy unveiled a series of “preferred shares” marketed with fun names such as “Strike,” “Strife” and “Stretch.” Investors receive a regular cash dividend ranging from 8 percent to 11 percent for a set period.
The arrangement may sound similar to a bond in a traditional company, such as an airline that pays out proceeds from ticket sales to finance more jets.
But buying Bitcoin and waiting for it to go up, as is Strategy’s mission, does not leave any money with which to pay cash dividends. The money can be easily produced only when Bitcoin is up, because Strategy’s stock rises with it. The cycle breaks when Bitcoin is down.
Despite that dynamic, Mr. Saylor has talked up the investments as safe and boring. “It’s not quite a high-yield bank account,” he told a podcast last fall, “but you would be pretty close.” (In reality, the price of the shares has swung up, down and sideways. Total loss is also possible, which isn’t the case at federally insured banks.)
Alexandre Laizet, deputy chief executive of the Blockchain Group, consulted with Mr. Saylor before starting a publicly traded European company with similar funding arrangements. Mr. Laizet calls it “ a major breakthrough in traditional finance.”
“I mean, of course,” he added, “we know that it’s not a bank account.”
What Could Go Wrong?
The pessimistic view on Mr. Saylor and Strategy is not exactly hard to unearth.
For one, investors are skeptical of Mr. Saylor’s checkered résumé. In 2024, he agreed to pay $40 million to settle lawsuits by the District of Columbia that accused him of evading local income taxes and bragging about it. (He disputed that and said he had settled “to avoid the continued burdens of the litigation.”)
Prominent investors and short-sellers, including James Chanos, famed for spotting Enron, have repeatedly rung the alarm. Among their concerns are that Strategy’s market worth, which peaked above $120 billion last summer, has regularly been higher than the sum of its Bitcoin.
That suggests that even if it liquidated all its holdings, it would be short of paying back shareholders, let alone the debt.
Standard & Poor’s, the credit agency, in December reassigned Strategy a junk rating.
S&P has pointed out that in the first half of 2025, Strategy’s $8.1 billion in earnings was entirely composed of rough price appreciation on paper of its Bitcoin, rather than traditional corporate earnings.
“If Bitcoin goes to zero tomorrow,” Mr. Saylor said at a December event in Miami, “it doesn’t matter whether I own 1 percent or 2 percent or 3 percent or a half-percent of it. It’s irrelevant.”
Further pressure is forming. The company’s stock is down by half since early October, when President Trump’s trade tussle with China set off a 24 percent spiral for Bitcoin.
The value of Strategy’s Bitcoin holdings dropped $17 billion in the fourth quarter, according to company disclosures.
As of this month, Strategy owes $21 billion to its lenders and preferred shareholders.
It is on the hook to pay more than $844 million to investors in the next year.
Bigger payouts loom. As soon as next year, Strategy’s convertible debt holders — the ones who lent money for as little as zero percent interest — will expect to swap into stock that Strategy had promised would be worth as much as $672 a share.
If it doesn’t trade at that level — it is currently around $171 — Strategy will have to find money to bridge the difference. In the next three years, $5 billion of such loans are due.
Mr. Saylor is already backing off his die-before-selling Bitcoin ways. Last month, Strategy announced that it had issued more stock again — but, in a turnabout, used the money to begin to stockpile more than $2 billion in dollars as a safeguard. Its chief executive, Phong Le, said on a crypto podcast that “we would sell Bitcoin if we needed to,” a move that Mr. Saylor separately described as “rational.” The company hasn’t yet.
Some are sticking by Mr. Saylor. “To deny that this is the future,” said Ed Juline, a former Strategy executive, “is the same as saying the internet is a fad.”
At Mr. Saylor’s villa on New Year’s Eve 2025, there was no big bash to equal the last. One of the previous year’s attendees recalled that Mr. Saylor had told a group that he would hold the next festivity only when Bitcoin reached $1 million. It recently traded around $95,000.
Mr. Saylor’s long-term prediction is $13 million by 2045.
Sophia June contributed reporting.
Rob Copeland is a finance reporter for The Times, writing about Wall Street and the banking industry.
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