Michael Saylor.

Before bitcoin

Michael Saylor grew up in a US Air Force family and went to the Massachusetts Institute of Technology (MIT) on an Air Force scholarship, he says, taking degrees in aeronautics and astronautics and in science, technology and society. After working as a consultant and then for the chemical company DuPont, he founded MicroStrategy in November 1989, at 24. It made business intelligence software, which helps companies analyse their data. Sanju Bansal, who joined in 1990, was later called a co-founder by the SEC. MicroStrategy’s shares began trading on the Nasdaq stock exchange in June 1998.⁠^{[1][2][3][11][4]}

In March 2000, at the height of the dot-com boom, MicroStrategy said it would restate its results for 1998 and 1999, and its shares lost more than 60% of their value in a day. That December the US Securities and Exchange Commission (SEC), which regulates the stock market, brought civil fraud charges against Saylor and two other executives. It alleged that the company had overstated its revenue and earnings and should have reported losses from 1997 onwards. Without admitting or denying the allegations, the three settled. Saylor agreed to give up $8.28 million and pay a $350,000 penalty. The agreement, he said, “fully concludes the Commission’s inquiry”.⁠^[4][5][6]

He stayed in charge, and in 2012 wrote The Mobile Wave, a book about how mobile computing would change business and everyday life. Bitcoin did not impress him. In December 2013 he posted on Twitter: “#Bitcoin days are numbered. It seems like just a matter of time before it suffers the same fate as online gambling.” He had thought governments would ban it, he said later, and by 2020 he had forgotten writing it. “I literally forgot I ever said that,” he told a podcast host.⁠^{[11][7][9][8]}

Turning to bitcoin

The pandemic changed his mind. In 2020 MicroStrategy had about $500 million in cash it did not need, and Saylor no longer saw cash as a safe place to keep it. “I went down the rabbit hole,” he told CoinDesk. He read essays by bitcoin’s advocates, listened to podcasts about it and, in CoinDesk’s words, lost himself in the “media empire” of Andreas M. Antonopoulos, the author of Mastering Bitcoin. “I want something that I could put $425 million into for 100 years,” he said.⁠^[10]

On 11 August 2020 MicroStrategy announced that it had bought 21,454 bitcoins for $250 million and made bitcoin the main holding in its treasury reserve, the money a company keeps rather than spends on running the business. Saylor pointed to the pandemic, governments’ stimulus spending and political uncertainty, which he said “may well have a significant depreciating effect on the long-term real value of fiat currencies”, money such as the dollar that governments issue. “Bitcoin is digital gold – harder, stronger, faster, and smarter than any money that has preceded it,” he said.⁠^[11]

It kept buying. In December 2020 it borrowed $650 million by selling convertible notes, loans that lenders can later swap for shares, and said it would put the money into bitcoin. From 2021 it also sold new shares on the stock market, a little at a time; until 2025, its annual report says, it relied mainly on selling shares and convertible notes to pay for its bitcoin. On 8 August 2022 Saylor handed the chief executive’s job to Phong Le, the company’s president, and became executive chairman, so that he could “focus more on our bitcoin acquisition strategy and related bitcoin advocacy initiatives”.⁠^{[12][13][19][14]}

That month the District of Columbia’s attorney general sued him under the city’s False Claims Act. The suit alleged that Saylor had lived in Washington, DC, for more than a decade while claiming to live in Florida, which has no income tax, and so evaded more than $25 million in tax; MicroStrategy was accused of helping him. In June 2024 the two sides settled for $40 million, which the attorney general called the largest income tax fraud recovery in the District’s history. The settlement records that Saylor and the company deny breaking the law and admit no wrongdoing, and Saylor paid the full sum himself. “Florida remains my home today, and I continue to dispute the allegation that I was ever a resident of the District of Columbia,” he said.⁠^{[23][24][25][26][27]}

Strategy

In October 2024 the company set out a “21/21 Plan” to raise $42 billion over three years, half by selling shares and half from fixed-income securities such as bonds, to buy more bitcoin. In May 2025 it doubled the target to $84 billion. On 5 February 2025 it began calling itself Strategy, with the bitcoin symbol ₿ as its logo, and described itself as “the world’s first Bitcoin Treasury Company”. That year it added five kinds of preferred stock, shares that pay a dividend before ordinary shareholders get anything, which it calls “digital credit”. On 11 August 2025 it changed its legal name to Strategy Inc.⁠^{[15][16][17][18][19][20]}

Strategy reports its purchases in filings with the SEC, so its total changes from week to week. In a filing on 12 October 2026 it said it held 848,250 bitcoins as of 11 October, bought for about $64 billion in all: about 4% of the 21 millionSupply cap (21 million)Bitcoin's rules halve the new supply every 210,000 blocks, so issuance slows towards zero. The total approaches 21 million without quite reaching it. bitcoins that can ever exist. It has sold a few. In December 2022 it sold 704 while buying more, to offset gains for tax, CoinDesk reported; between late May and early July 2026 it sold 3,620 and, its filings say, used the money to pay dividends on its preferred stock. Its annual report warns that holding so much of one asset “enhances the risks inherent in our bitcoin strategy”. Saylor’s shares carried 32.9% of the votes at the company in September 2026.⁠^{[21][39][40][41][19][22]}

The debate over Strategy

Strategy’s approach has drawn critics. The short seller Jim Chanos argued in 2025 that the company should not be valued above the bitcoin it owns, and that investors should simply buy bitcoin instead; he called Saylor’s case for a higher value “financial gibberish”. The gold investor Peter Schiff said the high dividends promised on Strategy’s preferred shares “will never actually be paid”, and called one of them “the most obvious Ponzi”. Phong Le, Strategy’s chief executive, has said the money raised goes into bitcoin, not dividends: “It’s not like we’re taking the proceeds, and we’re then using those proceeds to pay out dividends.”⁠^{[28][30][32][31]}

Saylor answered that Chanos did not understand Strategy’s business: “We’re actually the largest issuer of Bitcoin-backed credit instruments in the world.” He has also argued that its shares are easier for many investors to own than bitcoin itself, Yahoo Finance reported. Jeff Dorman, chief investment officer of the crypto fund manager Arca, pointed out in 2025 that none of Strategy’s debts include terms that would force it to sell bitcoin.⁠^[29][30][32]

Saylor has urged others to follow. In December 2024 he made a three-minute presentation to Microsoft’s board arguing that it should hold bitcoin, CoinDesk reported; Microsoft’s shareholders then voted down a proposal to assess the idea, with 0.55% in favour. He also argued for a national reserve: “Bitcoin is manifest destiny for the United States,” he said in November 2024. In March 2025 President Donald Trump ordered the government to set up a Strategic Bitcoin Reserve, stocked with bitcoin it had confiscated in criminal and civil cases.⁠^{[34][33][35][36]}

His views on self-custodySelf-custody (non-custodial)Holding your own keys, so no company can freeze, lose or take your bitcoin. The alternative, a custodial service, holds them for you., people holding the private keysPrivate keyThe secret number that lets you spend your bitcoin. Whoever knows it controls the coins, so it must never be shared. to their own coins instead of leaving them with a company, drew criticism too. In October 2024, in an interview with Madison Reidy of the New Zealand Herald, he argued that bitcoin was safer with big regulated firms such as BlackRock and JPMorgan, and dismissed fears of government seizure as coming mainly from “paranoid crypto anarchists”. Critics included Vitalik Buterin, a co-founder of Ethereum, and Jameson Lopp, a co-founder of the bitcoin custody company Casa: “There are many long-term negative ramifications to convincing people to trust third-party custodians,” Lopp wrote. Within days Saylor posted: “I support self-custody for those willing & able, the right to self-custody for all, and freedom to choose the form of custody & custodian.”⁠^[37][38]