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Michael Saylor Just Blew Up His Own ‘Never Sell’ Philosophy to Save Strategy Stock. Here’s Why.

For years, Strategy ($MSTR) founder Michael Saylor was the ultimate champion of a crypto rule: buy Bitcoin (BTC-USD) and never sell it. His company hoarded nearly 850,000 Bitcoin, turning the firm into the largest corporate holder of the digital asset on Earth. Saylor famously preached that Bitcoin was a permanent store of value that should be locked away forever. But a harsh crypto winter has forced Michael Saylor to blow up his own “never sell” crypto philosophy.

With Bitcoin sitting more than 50% below its record high, Strategy has officially abandoned its strict buy-only rule. The company’s board just approved a new financial system called the Digital Credit Capital Framework. For the very first time, this plan gives management permission to sell up to $1.25 billion worth of its Bitcoin stockpile. The company plans to use the cash from these sales to build a U.S. dollar reserve, pay out dividends to investors, and handle its corporate debts.

There Are Limits to Holding Forever

This policy shift reveals a major flaw in Saylor’s original vision. While treating a volatile cryptocurrency like a permanent piggy bank sounds great during a market boom, real-world businesses have fixed bills that cannot be paid in crypto. Strategy faced growing pressure as its stock price tumbled near a 52-week low. Investors have been pulling away from crypto to chase the booming artificial intelligence market.

To make matters worse, a crash in Strategy’s preferred stock created a funding crisis. The company owes massive annual dividend and interest payments of about $1.76 billion. Because it ran low on cash, the firm actually quietly sold 32 Bitcoin in May, just to pay its bills. That small sale was a clear warning sign. Now, by opening the door to billion-dollar liquidations, the business is admitting that a pure “never sell” strategy is impossible to maintain when a market downturn hits hard.

Strategy Aims to Protect the Corporate Structure

To stop its stock from sliding further, Strategy is launching a $2 billion buyback program. The firm will split that money evenly, spending $1 billion to buy back its common stock and another $1 billion to rescue its struggling preferred shares. Management explains that this move turns the business into an active capital manager rather than a passive crypto vault.

Wall Street actually cheered the announcement, sending the stock up over 11% as investors felt relieved that the company is taking steps to stay stable. Still, the irony is hard to ignore. Michael Saylor spent years telling the world that cash was trash and Bitcoin was the only asset worth holding. Now, his own company is selling off its precious Bitcoin just to stack up billions of plain old U.S. dollars.

Is Strategy Stock a Buy, Hold, or Sell?

According to TipRanks, Strategy (formerly known as MicroStrategy) stock has a consensus Strong Buy rating among 12 Wall Street analysts. This rating is based on 10 Buy and two Hold ratings assigned in the past three months. The average 12-month MSTR price target of $291.92 implies 212.6% upside from current levels. (See MSTR stock forecast)

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Annika is an Editor and Writer at TipRanks. She delivers in-depth company analysis and market commentary on stocks & cryptocurrencies listed on NASDAQ, NYSE, LSE, and many others. She previously worked at the firm as a TV anchor and market analyst, where she gained extensive experience translating fast-moving news into high-quality video content for a global audience. Annika draws on more than five years of experience in the financial domain. Her academic foundation comes from the London School of Economics and Cass Business School, where she studied Accounting & Finance. She sharpened her technical skills within the Investment Banking Division at Morgan Stanley before moving into fund management at AlmaStone. Driven by a passion for clarity, Annika founded Finpact, an educational platform designed to make complex financial concepts easy for everyone to understand. She focuses on keeping her research-led content simple and crisp. Her goal is to provide actionable insights that help investors make better decisions in both the traditional stock and cryptocurrency markets. Outside of her financial passions, Annika enjoys experimenting with new recipes in the kitchen, doing activities with her dog, and traveling.