Strategy (formerly MicroStrategy) faces mounting scrutiny as executive chair Michael Saylor aggressively markets its 11.5% dividend-yielding preferred shares (STRC), despite the company’s $7bn unrealized Bitcoin losses and 60% common stock plunge. The STRC campaign, criticized for blurring SEC compliance lines, positions the securities as a lifestyle upgrade rather than addressing core financial weaknesses. $570mn in 2024 insider selling and out-of-the-money convertible bonds further highlight equity holder risks. While Trump’s proposed 401(k) asset relaxations may ease regulatory pressure, Strategy’s reliance on perpetual capital raises—rather than operational profitability—remains a red flag for investors.