From Dot-Com Startup to Bitcoin Giant

Michael Saylor co-founded MicroStrategy in 1989. Through the 1990s the firm landed data-mining deals with McDonald's and others, and went public in 1998

Freshly-rebranded Strategy—formerly known as MicroStrategy (MSTR)—has shifted from being an enterprise software firm that sells business-intelligence (BI) tools to the world’s largest corporate owner of bitcoin. It holds about 581,000 bitcoins, worth around $63 billion, which is significantly higher than its annual software revenue of about $463 million. (All data here and below are as of early June 2025.)

Founder and CEO Michael Saylor calls the company a “Bitcoin Treasury Company,” a moniker the early 2025 name change makes explicit. To fund this hoard, Strategy has issued waves of zero-coupon convertible notes and new equity, turning itself into a leveraged bet on "digital gold."

Key Takeaways

From DotCom Startup to Bitcoin Giant

Michael Saylor co-founded MicroStrategy in 1989. Through the 1990s the firm landed data-mining deals with McDonald’s and others, and went public in 1998, briefly making Saylor a paper billionaire during the dot-com boom. After nearly going bankrupt because of a 2000 accounting scandal that resulted in a U.S. Securities and Exchange Commission settlement, the company steadily pivoted toward cloud analytics.

Fast-forward to August 2020, when Saylor first deployed some $250 million of idle cash into bitcoin, citing cash-debasement fears.

Multiple follow-on buys—financed first with cash, then with debt—turned the firm into “Wall Street’s bitcoin proxy.” The company's metamorphosis was completed with Strategy's name change, complete with an orange palette inspired by bitcoin.

Saylor champions his “infinite money glitch,” arguing that borrowing cheaply against stock to buy scarcer bitcoin offers shareholders leveraged digital gold exposure. Other high-profile companies are looking to follow Strategy's Bitcoin treasury playbook, with both Trump Media & Technology Group (DJT) and GameStop Corp. (GME) announcing massive fundraising in 2025 to do so.

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How Strategy Finances Its Massive Bitcoin Treasury

Strategy rarely pays cash for coins anymore. Instead, MSTR prefers to issue zero-coupon convertible notes with generous conversion premiums, effectively providing free money unless the stock tanks. It had already raised billions of dollars this way, part of a pattern that Bloomberg says has made convertible-arbitrage “Wall Street’s hottest trade.”

Issuing equity is another lever: during the first quarter of 2025 alone, Strategy sold $7.7 billion in new shares and then bought another 22,048 BTC at an average price of about $87,000.

To back this financial engineering, Strategy's slide deck often highlights the following metrics:

However, the math only works if Bitcoin continues to rise. A 30% slide in March briefly saddled the company with an unrealized $5.9 billion loss, rattling MSTR’s share price. Analysts warn that prolonged crypto winters would squeeze cash flow and could force asset sales or refinancings that dilute shareholder value. Its zero-coupon structure, furthermore, can let bondholders demand cash back if volatility spikes, creating a reflexive risk loop for shareholders.

Still, MSTR's recent inclusion in the Nasdaq-100 has meant that passive index funds tracking it have bought its shares, which will help cushion any potential drawdowns.

Warning

Investors looking to Strategy as a BTC play might be getting played themselves: At a market cap of $105.28 billion and bitcoin holdings at about $62.6 billion, that's almost a 70% premium over its BTC holdings. Compare that to most closed-end funds (where a 10% premium is pricey) or the Grayscale Bitcoin Mini Trust ETF (BTC), where our calculations show a 3.2% discount of its share price to net asset value per share. For every $1.00 you invest, MSTR provides $0.59 worth of BTC exposure, whereas for the BTC ETF, you get $1.03.

What Else Does Strategy Do?

Strategy continues to sell its Strategy One analytics suite—an AI-infused business intelligence and data platform, which has sustained growth in subscriptions. The company also runs Strategy World, an annual technology conference that, in 2025, spotlighted new generative AI features rolling into its platform.

Bottom Line

Strategy has morphed from a middling BI vendor into a leveraged macro bet on Bitcoin, wrapped around its still-functioning software business. If the crypto bull run persists, shareholders will reap the gains from embedded leverage in both equity and convertibles. If the tide turns, however, the same leverage will magnify