Sailor and MicroStrategy: Transforming Bitcoin Investment Strategies in the New Year

Over the past year, Michael Saylor’s position in the cryptocurrency ecosystem has significantly evolved. The CEO of MicroStrategy remains a key figure, but now his company faces different challenges and opportunities. If 2025 brought unprecedented growth, 2026 requires a rethinking of approaches.

Rise and Fall: How MSTR Shares Changed

Throughout 2025, MicroStrategy’s shares demonstrated impressive dynamics, increasing fivefold. This growth occurred despite the emergence of Bitcoin ETFs on the US market, which theoretically should have reduced the attractiveness of alternative instruments. However, at the start of 2026, the situation changed sharply. The company’s shares have shown negative returns since the beginning of the year, signaling significant difficulties in replicating last year’s success.

This turnaround is driven by several factors. First, Bitcoin’s volatility has noticeably decreased, reducing speculative opportunities. Second, the emergence of options on spot ETFs has opened investors alternative channels for exposure without needing to buy Saylor’s company’s shares. These circumstances have led to a critical reduction in the premium (multiplier) of MSTR relative to its net asset value — a measure reflecting how much higher the company’s market price is compared to its actual assets.

Preferred Shares: A New Capital Raising Mechanism

In response to these difficulties, MicroStrategy launched an ambitious program to issue preferred shares. This year, the company issued four series of such securities: STRK, STRF, STRD, and STRC. This initiative has attracted $4.6 billion in gross proceeds from primary offerings.

Three out of four issues demonstrated high appeal to investors, providing double-digit returns. For MicroStrategy itself, these preferred shares serve as a tool to increase Bitcoin holdings without traditional dilution of core capital. The company also extended this mechanism internationally, issuing preferred securities denominated in euros for the European market.

Bitcoin Strategy in a Competitive Environment

Saylor’s company’s behavior reflects a broader market evolution. When ETFs first appeared, they seemed a threat to specialized investors. However, multi-instrumentality — the availability of multiple ways to gain exposure — has become a market reality. MicroStrategy is adapting, transforming its role from a purely speculative instrument into a more complex financial mechanism.

Thus, Michael Saylor’s story in 2026 is not a tale of decline but a story of reorientation. The company is seeking new ways to create value in a context where the traditional premium is dissolving.