Michael Saylor's Strategy is abandoning its "Never sell your Bitcoin" mantra as cryptocurrency losses pressure the company's balance sheet. The software firm, which amassed over 600,000 Bitcoin tokens while prices soared, now faces mounting stress after digital assets lost more than half their value from peak levels.

Strategy unveiled a turnaround plan Monday authorizing up to $1 billion in share buybacks and launching a $1.25 billion monetization program funded through Bitcoin sales. This marks a dramatic shift from Saylor's original vision of transforming the company into a Bitcoin proxy vehicle. The move follows a cascade of funding strategies: initial cash purchases evolved into stock sales, then convertible bonds and high-yield preferred shares.

Bitcoin's decline below the psychological $60,000 threshold has hammered Strategy's stock price and depleted its cash reserves. Jeff Dorman of crypto asset manager Arca noted the company has "effectively kicked the can down the road" while each capital structure component competes internally.

Saylor maintains the long-term story remains intact despite the tactical retreat. The pivot reflects mounting pressure on crypto-focused businesses as the digital asset market faces its sharpest correction since the 2022 downturn, forcing even the most vocal Bitcoin bulls to reconsider their positions.