Michael Saylor transformed Strategy from a business intelligence company into the world's largest corporate Bitcoin holder.
Saylor's belief redefined corporate strategy, turning volatility into opportunity through long-term dollar-cost averaging.
Despite concerns about dilution and debt, his approach set a standard for institutional Bitcoin adoption.
Saylor's strategy manual emphasizes research, perseverance, risk management, and long-term thinking in Bitcoin investment.
In August 2020, Michael Saylor transitioned from a tech executive to a symbol of corporate cryptocurrency adoption.
For a long time, Saylor was known as the co-founder and CEO of the enterprise software company Strategy (formerly MicroStrategy), boldly entering the cryptocurrency space by allocating $250 million in cash to purchase Bitcoin (BTC).
He cited a weak dollar and long-term inflation risks as the fundamental reasons for this strategic move. Incidentally, this marked the largest acquisition of Bitcoin by a publicly traded company at the time, setting a new precedent.
Within months, Strategy expanded its holdings: adding $175 million in September, $50 million in December, and issuing $650 million in convertible bonds, bringing its Bitcoin holdings to over $1 billion.
He views Bitcoin as a "store of value," likening it to "Manhattan in cyberspace," a scarce and indestructible asset.
This move was both praised and criticized. Skeptics called it reckless, while supporters saw it as a bold innovation at a time when few dared to include Bitcoin on their corporate balance sheets. But for Saylor, it was not a gamble; it was a carefully crafted hedge against monetary uncertainty and a signal that digital assets would reshape capital strategies.
Did you know? In 2013, Saylor tweeted that Bitcoin's days were numbered, predicting it would "go the way of online gambling." This tweet resurfaced in 2020, coinciding with his transformation of Strategy into the largest Bitcoin holder among publicly traded companies. He later referred to it as "the most expensive tweet in history."
From the initial entry point, Saylor doubled and even tripled down on his belief in Bitcoin. He used structured financial instruments to expand his holdings, shaping Strategy into a "Bitcoin treasury company."
It all began with a financial report conference call in July 2020, when Saylor announced plans to explore alternative assets like Bitcoin and gold instead of holding cash. He implemented the plan through quarterly Bitcoin purchases, rapidly expanding his holdings to tens of thousands of coins at a favorable cost basis.
By early 2021, Saylor had borrowed over $2 billion to expand his Bitcoin position, a radical stance driven by conviction rather than speculation. He articulated a vision of long-term holding, stating that Strategy would hold its Bitcoin investments for at least 100 years.
Despite Bitcoin's extreme volatility, soaring from $11,000 in 2021 to $64,000, then plummeting to nearly $16,000 by the end of 2022, Saylor remained steadfast. To support the claim that Bitcoin is the pinnacle of monetary structure, his team employed dollar-cost averaging strategies to increase holdings during price declines.
Saylor's strategy paid off: his company's stock price soared, often outperforming Bitcoin itself. By the end of 2024, Strategy's stock returns were multiples of the S&P 500 index returns, with the enterprise viewed as a leveraged cryptocurrency proxy rather than a software company.
Saylor's fervor evolved from a bold entry to dominating corporate Bitcoin demand, changing market dynamics purely through scale. By early 2025, Strategy held over 2% of Bitcoin's total fixed supply, approximately 500,000 BTC.
Year-to-date, Strategy has acquired over 150,000 BTC at an average price of about $94,000, bringing the market value of its holdings to over $50 billion.
These large-scale allocations exert structural pressure on Bitcoin's limited supply, with corporations now competing for the scarce asset. Saylor set a benchmark that other companies began to follow. In just the first five months of 2025, institutional and corporate Bitcoin purchases exceeded $25 billion.
This scale changed Strategy's identity: software revenue was overshadowed by Bitcoin's impact on valuation. The equity-raising strategy of issuing stock and debt to fund purchases was scrutinized as recursive: if Bitcoin falls, debt could burden the company; if stock is overly diluted, investor confidence could wane.
In June 2025, Strategy purchased an additional 10,100 BTC for $1.05 billion, spending nearly $42 billion in total on Bitcoin. The company's model is now replicable, but systemic risks are also increasing.
Saylor's transition from tech CEO to architect of a crypto treasury has made him a polarizing figure and inspired imitators. His radical strategy manual not only redefined Strategy's valuation but also reshaped the broader narrative of institutional adoption.
Did you know? Saylor revealed that before converting company assets to Bitcoin, he personally purchased 17,732 BTC with his own funds, worth nearly $175 million at the time. This gave him enough confidence to push for corporate allocation at Strategy.
Saylor shows no signs of slowing down. Strategy continues to double down on Bitcoin, even funding new purchases through convertible debt and other innovative instruments. With the halving cycle tightening supply and institutional interest accelerating, Saylor positions Bitcoin not just as a store of value but as a corporate treasury standard.
Looking ahead, the key questions are whether more companies will follow Strategy's example, how regulatory frameworks will impact corporate adoption, and whether Bitcoin's function will be limited to balance sheets or extend to other areas of the financial system. If Saylor's theory is correct, he may not only be remembered as a bold CEO but also as a key player in fundamentally changing Bitcoin commercial financing.
Saylor's journey is unique, but anyone exploring Bitcoin can draw practical lessons from his approach:
Do your research before investing: Saylor studied Bitcoin fundamentals for months before investing. For newcomers, this means avoiding hype and starting with authoritative sources, white papers, and professional analyses.
Think long-term: Saylor had no intention of making quick profits. For individuals, this means only investing money you can hold through volatility, rather than trying to time the market.
Risk management is crucial: Strategy's borrowing to buy Bitcoin is a dangerous but bold move. Retail investors should be more cautious, avoiding excessive debt and treating cryptocurrency as part of a larger investment portfolio.
Have conviction but stay flexible: Over the years, Saylor methodically planned purchases, but he doubled down on Bitcoin even during downturns. For beginners, dollar-cost averaging can be a useful strategy.
Separate personal beliefs from corporate strategy: Not everyone has a company backing their Bitcoin bets. Saylor combined personal holdings with Strategy's treasury. For individuals, it's best to clearly distinguish between personal savings and speculative investments.
Even if you don't have Saylor's wealth, you can still apply some of his strategies to better navigate Bitcoin, such as doing your own research and maintaining patience and discipline.
Related: Alex Thorn: There is a "great opportunity" for the U.S. to form a strategic Bitcoin (BTC) reserve by the end of the year.
This article does not contain investment advice or recommendations. Every investment and trading involves risks, and readers should conduct their own research when making decisions.
Original article: “Michael Saylor's Bitcoin (BTC) Obsession: How It All Started”
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