Strategy (formerly MicroStrategy) founder Michael Saylor may well have lost more than $4 billion of his own money in the last six months thanks largely to declines in the price of bitcoin (BTC) and his company’s MSTR stock.
Indeed, Protos has examined Forbes’ most recent estimate of Saylor’s personal wealth and found it to be likely correct — albeit incomplete — based on Saylor’s limited public disclosures.
As of May 2, 2025, Saylor owned 19,616,680 shares of Strategy class B common stock, a 10:1 supervoting class of MSTR that empowers him with 43.58% voting power over the company.
Worth over $3.9 billion as of Friday’s closing price, this is a 52% drop from its $8 billion value six months ago. Despite this, Saylor’s class B equity remains his largest source of personal wealth.
Although Strategy didn’t disclose Saylor’s class B ownership in its latest quarterly report, his class B ownership is likely unchanged. Companies typically don’t provide individual breakdowns of major executive ownership unless there’s a significant change.
As further evidence, Saylor hasn’t filed a Form 3 or 4 to disclose insider transactions with the Securities and Exchange Commission since April 2024.
In summary, although only Strategy’s own executives and board members possess real-time knowledge of Saylor’s class B ownership, it’s probable that he still owns the same 19,616,680 shares, at least for the purposes of estimating his net worth based on public information.
Michael Saylor’s non-Strategy assets
Saylor also owns various other assets, including tens of millions of dollars worth of real estate and yachts. He also owns many valuable, single-word .com domains.
He’s also derived wealth from sales of regular, class A common stock. During the month of April 2024, for example, he exercised significant quantities of MSTR convertibles and then immediately sold at least $370 million worth of the stock.
Saylor then continued to sell a few tens of millions more to finish a pre-disclosed plan to sell up to 400,000 shares. The same pattern didn’t repeat in April 2025.
It’s not clear what Saylor did with the proceeds of these April 2024 sales. He could have purchased more BTC, spent the cash, donated it, saved it, or otherwise used it for a variety of purposes.
Finally, he also owns a substantial quantity of bitcoin (BTC) on a personal basis, outside of Strategy’s corporate treasury.
In August 2024, Saylor admitted to owning 17,732 BTC, although that quantity might have changed substantially since his last disclosure. If — and only if — that quantity is unchanged, Saylor would own $1.6 billion worth of BTC today.
Putting it all together, Saylor likely owns more than $3.9 billion worth of Strategy class B stock, more than $1.6 billion worth of BTC, at least tens of millions of dollars worth of real estate, untold millions of dollars worth of internet domains, and unknown quantities of non-public assets such as private equities and artwork.
In other words, he probably owns at least $5.5 billion worth of Strategy equity and BTC, plus extra assets.
Read more: Michael Saylor says bitcoin credit now has a yield curve — thanks to him
Bloomberg, Forbes, and unknown estimates
As of November 17, Forbes staff estimates Saylor’s worth at $5.9 billion — a 41% decline since its $10.1 billion estimate six months ago.
Forbes provides minimal disclosure as to the source of assets they consider. Still, its estimate seems to include his likely holdings of class B stock and BTC, plus an extra $400 million from other asset categories.
Although no one knows except Saylor himself, if it’s true that he’s has lost $4.1 billion worth of value from the 52% decline in his class B holdings, plus another $200 million loss from the 11% decline in his BTC, his six month loss might indeed come to $4.2 billion.
Moreover, he might have actually enjoyed some appreciation in his real estate, art, boats, or other non-public assets.
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Source: https://protos.com/michael-saylors-wealth-sheds-4b-as-mstr-and-btc-slide/
