Note that in early August 2022, Saylor ceased to be MicroStrategy’s CEO. He is now executive chairman of the company, but his influence within the organisation has not diminished. And while Sailor holds 16 per cent of all the company’s shares, he also holds 68 per cent of the voting power. Consequently, he has the final say on certain matters.

Distribution of votes at MicroStrategy

Michael himself has also reiterated his desire to continue to focus on the first cryptocurrency connection. Here’s his quote from earlier this month.

In my role as executive chairman, I will be able to focus more on our BTC acquisition strategy and related cryptocurrency protection initiatives, while Fong as CEO will be empowered to manage corporate operations.

MicroStrategy acquired 129,698 BTC for the equivalent of $3.975 billion, with this amount of cryptocurrency now valued at $2.604 billion. In other words, the giant is now down 34.5 per cent on its own position.

MicroStrategy’s bitcoin buying chart

Saylor has essentially become the leader of the so-called Bitcoin cult. He actively promotes the hodla strategy and refuses to sell the coins at the company’s disposal. Negative episodes have also happened to him. Specifically, in 2021, Michael explicitly advised his own fans to sell all of their assets in order to acquire BTC. As you can understand from the current market, it was far from a good idea.

Now a MicroStrategy representative has been accused of possible tax evasion. And the case has been announced by Washington Attorney General Karl Racine himself.

What MicroStrategy’s Michael Saylor is being sued for

According to a tweet Racine released last night, MicroStrategy allegedly helped Seylor “evade paying hundreds of millions of dollars in taxes he earned while living in D.C.” Karl also described Michael Saylor as “a billionaire technology company executive who has lived in D.C. for more than a decade, yet has never paid the income tax of the relevant region.”

As Decrypt points out, Saylor is accused of using an “elaborate scheme” to evade taxes in D.C. between 2014 and 2020. And while Michael allegedly claimed to be a resident of Florida – a state without an income tax – he himself was preliminarily based in Washington DC for most of the year. In addition, sources claim that Saylor openly talked about the scheme.


That is, if Sailor lived fully in Florida, there would be no questions about him. But he allegedly lives in Washington, D.C., which means he must pay taxes according to state law.

Former MicroStrategy executive Michael Saylor

Racine’s team investigated the allegations and found that Saylor had failed to pay at least $25 million in D.C. taxes. In addition, Michael had previously used MicroStrategy to file false W-2 forms stating that he allegedly lived in Florida.


As Racine suggests, the total amount of unpaid taxes and fines could be more than $100 million.


Saylor responded to what was going on with the following quote.

Ten years ago I bought a house in Miami Beach and moved there from Virginia. And although MicroStrategy is in Virginia, Florida is where I live, vote and serve as a juror. It is where my personal and family life is centered.

As Sailor added, he “respectfully disagrees with the D.C. position and hopes for a fair decision in court.”

In addition, MicroStrategy has responded to the situation and has decided to distance itself from the former executive.

The case concerns Mr Seylor’s personal taxation. The company was not responsible for his day-to-day affairs and had no control over his individual tax liabilities. Nor did MicroStrategy collude with Mr Seylor in the performance of his personal tax obligations.

MicroStrategy claims that the prosecutor’s allegations are “false”. They are therefore prepared to “aggressively defend themselves” against such attacks.

Former MicroStrategy executive Michael Saylor

Racine also accompanied the postings on Twitter with the following quote

Through this lawsuit, we’re calling the attention of residents and employers to the fact that if you want to enjoy all the benefits of living in our great city while refusing to pay a fair amount of taxes, you will be held accountable.

Note that Michael Saylor has previously explicitly hinted that if anything he is prepared to tell officials about the alleged loss of his bitcoins on the boat. Here’s his line from a January 2021 interview.

You can put this in your head, remember the damn private key. Oops, my bitcoins? I lost them in a boating accident. It’s kind of an exaggeration, but the gist is this: if you end up taking it too far, well, I lost it, it’s gone, sorry. Tax it.

It is worth noting that this statement has also turned up in the case file. The relevant part is highlighted in the screenshot below.

Moreover, during an interview on January 24, 2021, Saylor boasted that Bitcoin was an ideal tool for tax evasion. He claimed that BTC owners could tell their government to “fuck off” and claim the loss of bitcoin access keys, at the same time advising the authorities to tax it.

Proceedings against Michael Saylor and MicroStrategy


Michael Saylor's financial resources are likely to be enough to defend himself in court. However, such a case is a serious damage to the reputation of the entrepreneur and his company. Yes, BTC fans love the slogan that "taxes are theft". But it's one thing to say such a thing during a YouTube interview and another to justify yourself in court and prove that you didn't mean anything of the kind. So the next move is for the prosecutor's office to make, and it's sure to be an interesting one.


What do you think about it? Share your opinion in our millionaire cryptochat. We’ll talk about other topics there as well.