Bitcoin has always been a magnet for bold investors. Among them, one name keeps popping up—Michael Saylor, Executive Chairman of Microstrategy. Though Saylor didn’t start as Bitcoin’s biggest fan, his shift from skepticism to enthusiasm has put his company, Microstrategy, in the spotlight. With its massive Bitcoin holdings, MSTR has become a fascinating subject for financial analysts and casual cryptocurrency fans.
In this article, we’ll break down:
Let’s dive in.
Microstrategy has methodically accumulated Bitcoin, solidifying its position as a corporate crypto heavyweight. Below, we explore this timeline, year by year.
Here is the summarized table of MicroStrategy’s Bitcoin purchases grouped by year:
# | Year | BTC Purchased |
---|---|---|
1 | 2020 | 70,470 |
2 | 2021 | 53,921 |
3 | 2022 | 8,109 |
4 | 2023 | 56,650 |
5 | 2024 | 234,509 |
6 | 2025 | 81,785* |
* Figures are based on April 8, 2025 data and may change as Strategy buys more Bitcoin throughout 2025
In August 2020, Microstrategy shocked the financial world by announcing its initial purchase of 21,454 Bitcoin for $250 million. Over the following months, MicroStrategy doubled down, adding another 48,916 BTC through subsequent purchases.
This initial foray was fueled by Saylor’s belief that Bitcoin was a better store of value than cash. At the time, he described cash as a melting ice cube, arguing that Bitcoin offered protection against inflation and economic uncertainty.
If 2020 was the appetizer, 2021 was the main course. In 2021, the company purchased nearly 54,000 BTC, further solidifying its position as a corporate whale in the crypto market. Notable purchases included 19,452 BTC in February, a move made just as Bitcoin’s price surged to new highs.
The decision to acquire Bitcoin at such a rapid pace was not without critics, but Saylor remained undeterred. His famous tweet, “Bitcoin is hope,” expressed his conviction in its potential to change the world.
Saylor wasn’t shy about his bullish stance. In interviews, he often likened Bitcoin to a “technological phoenix,” arguing that it offered unparalleled security and long-term value.
By 2022, the crypto market had entered a bearish phase, but that didn’t deter Microstrategy. The company still managed to add over 8,000 BTC to its holdings. This period coincided with a bear market that saw Bitcoin’s price drop significantly, testing the resolve of even the most committed investors. The strategy was clear: buy during downturns to maximize future gains.
MicroStrategy remained steadfast, framing the downturn as an opportunity to accumulate more Bitcoin at lower prices. Saylor stepped down as CEO in August to focus exclusively on Bitcoin strategy, signaling his unwavering commitment to the cryptocurrency.
Despite market volatility, 2023 was another big year for MicroStrategy. The company purchased over 56,000 BTC, making significant additions during periods of price consolidation. MicroStrategy’s Bitcoin investment was no longer considered a gamble; instead, it was viewed as a calculated decision that other businesses were replicating.
Saylor continued to advocate for Bitcoin, emphasizing its potential as a digital asset and a hedge against inflation. His public appearances and interviews often highlighted the importance of thinking long-term in a market prone to short-term fluctuations.
In 2024, MicroStrategy went all in, acquiring 234,509 BTC. Following President Trump’s victory, Microstrategy purchased more Bitcoin, a profitable strategy as the price of Bitcoin went up. This year alone accounted for nearly 60% of its total Bitcoin holdings.
As of March 202e, MicroStrategy owns 528, 185 BTC. This staggering amount positions the company as the largest corporate Bitcoin holder and underscores its long-term commitment to the cryptocurrency.
MicroStrategy’s strategy paid off handsomely in late 2024 and early 2025. The company protected its cash reserves from inflation and realized significant paper gains as Bitcoin’s value has appreciated over the years. However, with uncertainties surrounding global markets, Microstrategy registered losses as the price of Bitcoin fell from its $100,000+ high to just under $85,000 in March 2025.
MicroStrategy, now Strategy, rebranded in February 2025 to reflect its shift toward a Bitcoin-focused identity. Michael Saylor’s strategy, initiated in 2020, involved holding Bitcoin as a treasury asset, viewing it as a better store of value than traditional assets. By early 2025, Strategy held over 500,000 Bitcoins, making this focus central to its identity. This prompted the name change and a new logo featuring a Bitcoin “B.”
While MicroStrategy’s Bitcoin holdings are impressive, Michael Saylor’s personal investments in Bitcoin are equally noteworthy. Saylor has revealed that he owns 17,732 BTC, purchased for $175 million at an average price of $9,882 per Bitcoin.
While many corporate leaders prefer to stay distant from their company’s investments, Saylor has demonstrated his commitment by investing his own money.
Saylor’s Bitcoin story is a tale of transformation. In 2013, he tweeted that Bitcoin’s days were numbered, predicting it would fade like online gambling. Fast forward to 2020, and he was singing a completely different tune.
What changed? According to Saylor, the COVID-19 pandemic was a turning point. With governments printing trillions of dollars to stimulate economies, he became concerned about the erosion of cash value. With its fixed supply and decentralized nature, Bitcoin seemed like the perfect antidote.
Saylor now describes Bitcoin as “the next Strategic Reserve Asset,” a way to preserve wealth in a world of inflation and uncertainty.
His conviction has made him one of Bitcoin’s most vocal advocates. He often appears on mainstream media to discuss its merits.
The Trump Dump refers to a price drop in Bitcoin (and stocks) following Donald Trump’s series of tariff announcements, causing market volatility. Before this, Bitcoin was around $85,000 in late March; by early April, it dropped to about $82,000.
For Strategy, holding approximately 506,137 Bitcoins could mean a loss of roughly $1.6 billion (528,185 × ($85,000 – $82,000)). However, considering earlier price drops from $97,000 in February to $85,000 by March, total unrealized losses might be higher, estimated at $5 to $8 billion, reflecting the volatility’s impact on Saylor’s mission.
Saylor aspires for Bitcoin to appreciate significantly, replacing gold as a store of value, potentially yielding high returns. However, the strategy risks substantial losses during price drops, especially with Strategy’s reliance on Bitcoin, amplified by debt-funded purchases, potentially affecting financial stability if prices continue to fall.
MicroStrategy’s aggressive Bitcoin acquisitions reflect its growing belief in cryptocurrency as a long-term store of value. With over 420,000 BTC in its portfolio as of 2024, it’s clear the company is betting on Bitcoin’s potential as an asset class, even amid volatility.
With more institutional investors following the Microstrategy plan, the future of Bitcoin in corporate treasuries seems increasingly inevitable. It signals a shift in how businesses view digital assets in investment and operational contexts.