Michael Saylor, Executive Chairman and co-founder of MicroStrategy (now Strategy) has pulled off one of the boldest financial moves in history, turning MicroStrategy into the biggest corporate holder of Bitcoin. What started as a simple bet in 2020 has now become a full-blown obsession, with the company holding nearly half a million BTC.
Saylor’s unwavering belief in Bitcoin has shaped MicroStrategy’s entire strategy, pushing the company to take on debt, sell shares, and invest billions—all in the name of accumulating more of the digital asset.
When did Strategy start buying Bitcoin?
2020
It all began on August 11, 2020, when MicroStrategy made its first Bitcoin purchase of 21,454 BTC for $250 million at an average price of $11,653 per Bitcoin. At the time, Saylor had already done a complete 180 on Bitcoin. He went from being skeptical to calling it the best store of value, even better than cash and gold.
And he wasn’t done. The company added 16,796 BTC in September 2020, which is valued at $175 million, followed by a massive buy in December, scooping up 29,646 BTC at $21,925 per Bitcoin, valued at $50 million. But Saylor wasn’t just using company cash. He took on debt, issued convertible and senior secured notes, and even sold MicroStrategy shares to buy more Bitcoin.
2021
In 2021, the company raised $650 million through senior secured notes and immediately used it to buy more Bitcoin worth $1 billion.
In 2021, Michael Saylor and MicroStrategy went all-in on Bitcoin, stacking up thousands of BTC through aggressive buying sprees. February was a standout month, with the company dropping over a billion dollars to snag nearly 19,500 BTC at an average price of $52,765 per coin. But they didn’t stop there.
As the months rolled on, they kept adding to their stash, making big purchases in May, June, and beyond. One of their best moves came in June when they secured 13,000 BTC for just $37,617 each—a bargain compared to later prices.
By the end of the year, they were still in the game, buying more in December with Bitcoin prices ranging from $49,229 to $59,187. Some called it reckless, others called it genius, but one thing was clear—Saylor was betting everything on Bitcoin, and he wasn’t looking back.
2022
In 2022, the crypto market took a massive hit. Bitcoin plunged below $16,000, shaking up the entire industry. Investors panicked, unsure of what was coming next. But Saylor didn’t budge. Instead of pulling back, he went all in.
Between February and December 2022, Bitcoin saw wild price swings, with major buys and sells recorded under Form K-8. In early 2022, BTC traded around $37,865, peaking at $45,714 in April when 4,167 BTC were bought. Prices then slid, with purchases at $20,817 in June, $19,851 in September, and $17,871 in December.
A notable sale of 704 BTC happened on December 22 at $16,776. Despite the drop, massive profits were still made, showcasing Bitcoin’s volatility and big-money moves in the market.
2023
By April 2023, MicroStrategy had accumulated over 140,000 BTC at an average price of $29,803 per Bitcoin. While many thought Bitcoin’s golden days were over, Saylor held his ground—and in the end, he was right.
In 2023, Bitcoin saw major price jumps, with big-money moves recorded under Form K-8. In March, 6,455 BTC were bought at $23,238, followed by more acquisitions in April, June, and July as prices climbed past $28,000. By September, BTC hit $27,053, with a massive 5,445 BTC purchase.
The rally continued, reaching $34,495 in October and $36,785 in November, with over 16,000 BTC bought. By December 27, Bitcoin surged to $42,110, with a staggering 14,620 BTC purchases worth $615.7 million. The year ended with massive gains, proving once again how volatile yet rewarding the crypto market can be.
2024
Fast forward to 2024 and 2025, and the buying spree has only gotten bigger. In November 2024, MicroStrategy made its largest Bitcoin purchase ever—55,500 BTC for $5.7 billion at $57,000 per coin.
Then came 11,000 BTC in January 2025 at $101,191 per Bitcoin, followed by another 20,356 BTC in February for $1.99 billion at $97,514 per Bitcoin.
In 2024, Bitcoin saw a rollercoaster ride, starting at $43,765 in February and soaring past $106,000 by December. Early in the year, massive buys at lower prices brought huge gains, with February and March trades seeing profits as high as 60%.
By mid-year, BTC hovered around $65,000-$74,000, with September’s surge to $60,408 bringing 37% gains. The real madness hit in November and December, as Bitcoin crossed $100K, but heavy sell-offs triggered sharp losses, with a 22% drop on December 23 alone.
By year-end, BTC had settled near $97,837, closing out a wild but highly profitable year for big players.
2025
Yesterday, on March 17, 2025, Strategy made the lowest Bitcoin purchase of 130 Bitcoin, which is valued at $10.7 million.
Now, as of March 2025, MicroStrategy holds 499,226 BTC, making it the single largest corporate Bitcoin holder. The company has spent $33.1 billion, with an average buying price of $66,380 per Bitcoin.
With Bitcoin currently trading above $82,589, MicroStrategy’s holdings are worth $35.9 billion, meaning they have an unrealized profit of $2.8 billion.
Michael Saylor’s Strategy (formerly MicroStrategy) just made history, becoming the first public company to own over 500,000 Bitcoin. Between March 17 and 23, it bought 6,911 BTC for $584.1 million at an average price of $84,529 per coin.
Now holding a staggering 506,137 BTC—worth $33.7 billion, the company funded this latest buy by selling 1.97 million MSTR shares for $592.6 million and 13,100 STRK shares for $1.1 million. Despite these sales, it still holds $3.57 billion in MSTR shares and $20.99 billion in STRK shares if more funds are needed.
As of March 31, Strategy added 22,048 BTC for $1.9 billion, bringing its total holdings to 528,185 BTC, now worth $43.84 billion at Bitcoin’s $83,000 price. The acquisition was funded by selling 3.65 million MSTR shares for $1.2 billion and 213,807 STRK shares for $18.52 million last week.
What is Strategy’s liquidation price?
The company is currently in profit of 25.36%, with the current profit valuation of $8.4 billion. But here’s the catch, if Bitcoin drops below $66,380, MicroStrategy’s entire Bitcoin investment would go into the red. That’s just a 20.23% price drop from current levels, which is not out of the question given Bitcoin’s volatility.
For Saylor, this isn’t just about making money, it’s something bigger. He sees Bitcoin as the future of money, like digital gold, and even calls it a financial revolution. Some think he’s a genius, others say he’s taking a huge risk, but there’s no denying one thing—no other company leader has ever gone this deep into Bitcoin. And as long as he’s running the show, MicroStrategy isn’t backing down.
Also Read: Crypto Price Today (March 18, 2025): Bitcoin Rejects $85k, SOL & XRP Drops
