Michael Saylor's company Strategy has weathered some of its toughest times since shifting to an all-Bitcoin portfolio in 2020, but its current financial structure is under unprecedented stress. The price of Bitcoin recently dropped to $58,000 on June 26, 2026, wiping out more than half of its all-time high of $126,000.
As a result, Strategy's unrealized losses have ballooned to over $13 billion on its 847,363 BTC reserves. Despite this, Saylor remains committed to the company's accumulation strategy and is not changing course.
In fact, he recently told shareholders that 'volatility tests every capital structure', and that Strategy would continue to act 'with transparency and determination'. This stance has been echoed by supporters of the model, who point to a 2022 precedent where the company held 130,000 BTC at a price under $20,000, yet did not sell.
However, not everyone is convinced. CryptoQuant recommends suspending purchases until cash reserves are replenished, and Strategy's financial structure faces significant challenges. Its preferred share STRC has fallen below $89, automatically triggering an increase in dividend payments to shareholders, which will add approximately $53 million in annual expenses.