In 2020, Michael Saylor changed his company forever. The head of Strategy, once known as MicroStrategy, took a bold step and bought Bitcoin. At that time, few big firms dared to hold crypto on their balance sheet. Saylor saw a chance to do something new.
He started by using $250 million of the company’s cash to buy Bitcoin. He explained that the dollar was getting weaker and that inflation could hurt long-term value. “Bitcoin is capital preservation,” he said, calling it “Manhattan in cyberspace.” The approach made headlines because it was the biggest Bitcoin purchase ever by a public company.
Not long after, Strategy added even more Bitcoin. The firm spent another $175 million in September 2020. By December, it bought $50 million more. That same month, the company raised $650 million through notes to buy even more Bitcoin. In just a few months, Strategy held more than $1 billion worth of the digital asset.
Some investors praised Saylor for being bold. Others said it was too risky. For Saylor, it was not a gamble. He called it a safe move against money losing value. His company had just changed from a software maker into something new.
Building a Bitcoin Treasure
Saylor’s idea was not random. During a July 2020 earnings call, he spoke about looking for better places to hold cash. He said Bitcoin and gold were on the table. Soon after, he put the idea into action with regular Bitcoin purchases.
By early 2021, Saylor borrowed more than $2 billion to buy even more Bitcoin, stating that they plan to hold their Bitcoin for “at least 100 years.” The company bought coins whenever prices dipped, a method called dollar-cost averaging.
Bitcoin prices jumped from $11,000 to $64,000 in 2021. By the end of 2022, prices fell near $16,000. Saylor did not back down. He used the lower prices to buy more coins. His company’s stock also climbed, at times beating Bitcoin itself.
By late 2024, Strategy shares had gained far more than the S&P 500. Investors began to see the company as less of a software firm and more of a Bitcoin play. Strategy had become a way for Wall Street to invest in crypto without holding coins directly.
Financing and Growth
By 2025, Strategy was no longer a regular software company. It held about 638,460 Bitcoin, nearly 2% of all the coins that can ever exist, according to Bitcoin treasury. Just recently, the company added 4,048 Bitcoin worth $449.3 million at an average cost of $110,981 per BTC.
Saylor’s purchases changed the market. In the first five months of 2025, companies and funds bought more than $25 billion worth of Bitcoin. His model was simple but huge. He raised money by selling stock and issuing debt, then used it all to buy Bitcoin.
In June 2025, Strategy added 10,100 Bitcoin for $1.05 billion. By then, the firm had spent nearly $42 billion on Bitcoin. Its software sales were small compared to the value of its Bitcoin stash. Some experts said the model was risky. If Bitcoin prices fell, the company’s debt could be a problem. If the company sold too much stock, investors might walk away.
Still, Saylor kept going. He showed no signs of slowing down. He found creative ways to keep buying coins, including the use of convertible debt.
Looking Ahead
Saylor now speaks of Bitcoin not just as a hedge but as a new standard for company balance sheets. He believes supply will get tighter as halvings cut new coin production. He also thinks more firms will copy his playbook.
The big questions now are about the future. Will more businesses follow Strategy’s example? Will Bitcoin just sit on balance sheets or move into other areas of finance?
No matter what happens, Saylor’s move has already changed the story of corporate investing. He turned his company into a Bitcoin giant and forced Wall Street to pay attention.
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