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Under executive chair Michael Saylor, Strategy (formerly known as MicroStrategy), the software firm turned bitcoin treasury vehicle, has captured the attention of the corporate finance world. The company’s pivot to bitcoin accumulation in August 2020 led to a surge in stock price and a growing audience of enthusiasts. However, recent developments have raised concerns among investors.
At its peak in late 2024, Strategy seemed to have found a winning formula. Saylor’s active online presence, filled with bold claims about bitcoin’s significance and the company’s success, created a positive feedback loop. But the magic has faded, with shares plummeting by 70% from their peak and significantly underperforming bitcoin. This raises doubts about the value Strategy brings to the table.
A recent announcement of a $1.4 billion equity raise for dividend obligations instead of bitcoin purchases has further fueled skepticism. The market reacted negatively, with shares dropping and questions arising about the company’s business model. The decision to prioritize dividend payments over bitcoin accumulation has left common shareholders in a tight spot.
Additionally, news of Strategy’s general counsel retiring and the struggle to regain investor trust have added to the company’s challenges. With convertible bonds trading below their value and a lack of capacity to buy bitcoin during downturns, Strategy’s future looks uncertain.
Management’s introduction of new metrics and unconventional strategies in a recent investor presentation has raised eyebrows. The company’s constant script changes and erratic behavior have tested investor patience. The disconnect between promises and results has become glaring, especially as the stock price continues to lag behind expectations.
In conclusion, Strategy’s corporate finance spectacle, led by Saylor, has lost its charm. Theatrics can only go so far, and the burden falls on ordinary shareholders. Investors are left wondering if there are any valid reasons to hold onto common stock in the face of uncertainty.
With Strategy’s future in question, investors must carefully evaluate their positions and assess the company’s path forward. The narrative of Strategy’s rise and fall serves as a cautionary tale in the world of corporate finance.

