Strategy's chairman, buying the trustless asset on borrowed trust
Michael Saylor co-founded MicroStrategy in 1989, two years after graduating from MIT. In March 2000 the company announced it would restate its results for 1998 and 1999, and in December 2000 the SEC brought civil fraud charges against Saylor personally, alongside co-founder Sanjeev Bansal and the firm’s former CFO, Mark Lynch. Saylor settled without admitting wrongdoing: an $8.28 million disgorgement and a $350,000 penalty.
For the next two decades he ran a business-intelligence software company that never regained its dot-com-era scale. Then, on August 11, 2020, MicroStrategy disclosed a $250 million purchase of 21,454 bitcoin, calling it “a dependable store of value… with more long-term appreciation potential than holding cash.” At the time, as the ownership map puts it, a bitcoin corporate treasury was still an experiment; the purchase is one of the data points weighed in asking whether Bitcoin’s whitepaper actually overturned the concept of money.
The 2020 purchase reversed a position Saylor himself had staked out seven years earlier.
Michael Saylor (tweet, December 19, 2013, 1:18:24 AM UTC)#Bitcoin days are numbered. It seems like just a matter of time before it suffers the same fate as online gambling.
He posted that in December 2013. Asked about it years later, after his own company had become bitcoin’s largest corporate holder, his answer was not a defense of the earlier view — it was that he had no memory of holding it:
Michael Saylor (The Pomp Podcast interview, September 16, 2020)I literally forgot I ever said that.
Satoshi Nakamoto’s whitepaper describes what it built in one sentence, in its own conclusion:
Satoshi Nakamoto (whitepaper, October 31, 2008, 6:10:00 PM UTC)We have proposed a system for electronic transactions without relying on trust.
Strategy assembled the largest corporate position in that asset by relying on nearly every form of trust a public company can call on. Beyond its common stock, it issued a series of preferred shares — STRK, STRF, STRD, STRC — paying fixed dividends funded from operations and further share issuance, not from the bitcoin itself, which earns no yield of its own. On October 27, 2025, S&P Global Ratings gave Strategy’s debt its first-ever assessment from a major agency: B-, six notches into speculative-grade territory, citing the company’s concentration in one volatile asset and the mismatch between dollar-denominated obligations and a non-dollar holding.
The company also trades at a premium to the market value of its own bitcoin — its “mNAV.” That premium is not a footnote; it is what funds the preferred dividends and what new equity issuances depend on to raise cash without selling coins. By August 2025 the premium was already compressing, and analysts were asking in public what a sustained bitcoin downturn would do to a financing structure built on it holding steady.
In 2026 the dependence became visible on the balance sheet itself. Between May 26 and 31, Strategy sold 32 bitcoin to help fund a preferred-dividend payment — a small amount, but the company’s first net reduction in holdings since the August 2020 purchase that started the buying. A month later, in the weekly reports of June 30 and July 6, it disclosed net sales of 1,363 and 2,225 bitcoin, about 3,588 in all for roughly $216 million, again to fund preferred dividends rather than issue new equity — the largest sale in the company’s history, and one made below its own roughly $75,476 average acquisition cost. Over those two weeks its holdings fell from 847,363 to 843,775. But an asset accumulated on the promise that it needs no one’s permission was, for the first time, being spent at a loss to keep a financing structure current.
The 2000 SEC settlement was not Saylor’s last regulatory encounter with the word “trust.” In June 2024, he and Strategy paid $40 million to settle a Washington, D.C. lawsuit alleging he had claimed Florida residency while actually living in the District, avoiding more than $25 million in income tax he owed between 2014 and 2020 — the largest income-tax-fraud recovery in the city’s history. He disputed the residency claim even in settling it.
Neither case is evidence that the asset thesis underneath his purchases is wrong; an accounting fraud from before Bitcoin existed and a personal residency dispute are not the same claim as “Bitcoin needs no trust.” What the two settlements show is narrower, and just as durable: the person who built the largest corporate case for an asset advertised as needing no one’s trust has twice settled authorities’ claims that he misrepresented the facts ordinary financial trust depends on.
Saylor has also become one of Satoshi Nakamoto’s more quoted admirers, in miniature. Reflecting on Satoshi’s disappearance, he compressed his reading into a single line: “Satoshi created a way, gave it away, and walked away.” Eighteen months later, on the whitepaper’s seventeenth anniversary, he returned to it in three words: “Thank you, Satoshi.” Both lines treat Satoshi’s absence as the gift rather than the mystery — a reading documented alongside dozens of others spanning Bitcoin’s history.
Saylor did not design Bitcoin’s protocol, and he did not found a rival chain the way most of the other founders profiled on this site did. His claim on Bitcoin’s history rests on a different kind of act entirely: turning a public company’s stock, its debt markets, and its own credit rating into a vehicle for accumulating the asset at a scale no government, fund, or individual outside Satoshi himself has matched. That the vehicle runs on exactly the trust — of shareholders, credit-rating agencies, and preferred-stock buyers — that the asset itself was built to make unnecessary is not incidental to the record. It is the most specific thing the record shows: whoever eventually holds bitcoin at Strategy’s scale, the terms on which they got there are part of what happened to it too.
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