Michael Saylor has turned his company into the biggest corporate holder of Bitcoin. What started in 2020 with a $250 million purchase has grown into a strategy that now controls more than 2% of Bitcoin’s total supply. For Saylor, the move was never about chasing quick profits. It was about protecting value in a world of inflation and changing money.
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Saylor Discovers Bitcoin
In August 2020, Saylor shifted from being a tech executive to becoming one of the loudest voices for Bitcoin. At the time he was running MicroStrategy, now renamed Strategy (MSTR), a software firm best known for business intelligence tools. Instead of leaving the company’s cash in dollars, Saylor decided to buy Bitcoin, calling it a better long-term store of value.
He put $250 million into the asset, then quickly followed with $175 million in September and $50 million more in December. By the end of the year, he even raised $650 million through convertible debt to expand the company’s position. He called Bitcoin “capital preservation” and once described it as “Manhattan in cyberspace.” Supporters called it visionary, while critics said it was reckless. Either way, it was the biggest corporate Bitcoin purchase the world had seen at that point.
Saylor Keeps Buying
The early purchases were just the beginning. In earnings calls during 2020, Saylor announced that he was moving beyond cash and into assets like Bitcoin on a permanent basis. From there, the company kept buying more every quarter, often during price dips.
By early 2021, Saylor had borrowed billions of dollars to expand the holdings. He made clear that the plan was to hold the Bitcoin for decades, saying it was a 100-year bet. Even as the price swung wildly, from $64,000 highs in 2021 to lows near $16,000 in 2022, Saylor never backed off. He used the downturns to keep buying more.
The gamble made Strategy’s stock soar. Investors no longer saw it as a simple software company. They saw it as a corporate Bitcoin proxy. By 2024, its stock had outperformed the S&P 500 several times over, showing how closely the company’s fate was tied to Bitcoin.
Saylor Changes the Corporate Game
By 2025, Strategy held more than 2% of all Bitcoin in existence, which meant nearly half a million coins. Just this year alone, the company bought over 150,000 BTC at an average price close to $94,000. That put the holdings at more than $50 billion in value.
This scale forced other companies to pay attention. In the first half of 2025, corporate and institutional Bitcoin purchases totaled more than $25 billion, and many pointed to Saylor as the spark. He showed that corporate treasuries could be used not just for safe bonds or stock buybacks but also for cryptocurrency.
Critics worry that raising debt and issuing stock to buy Bitcoin is dangerous. If prices fall too far, the debt burden could weigh heavily on the company. If too much new stock is issued, shareholders could be diluted. Still, Saylor has pressed on, even buying more than $1 billion worth of Bitcoin in June 2025.
What Next?
Saylor shows no sign of slowing down his BTC buying. He continues to finance new Bitcoin buys with creative tools like convertible debt. He believes halvings and growing institutional demand will only make Bitcoin scarcer and more valuable. For him, it is the new standard for corporate balance sheets.
The question now is whether other companies will follow. Some firms already hold small amounts of Bitcoin, but none have matched Saylor’s scale or conviction. If regulation becomes clearer and more institutions step in, Bitcoin could become a normal part of how big companies manage their money.
For investors and executives reading this, Saylor’s journey is full of lessons. He did his research before committing, he thought long term, and he stayed consistent even when prices collapsed. He also took risks that most retail investors would find too extreme.
Even if most people cannot buy Bitcoin the way Saylor did; patience, conviction, and careful risk management can matter more than timing the market.
Is MicroStrategy Still a Buy?
Wall Street is lining up behind Michael Saylor’s Bitcoin-driven vision. Based on 13 analyst ratings over the past three months, Strategy stock has been rated a Strong Buy. Out of those 13, twelve analysts have a Buy rating, none recommend a Hold, and just one has a Sell rating.
The average 12-month MSTR price target sits at $564.15, which implies a 70.72% upside from the recent price.
