MSTR Shareholders Told to Ride Out 'Pain' as Stock Sees Gains

Michael Saylor, co-founder and executive chairman of Strategy Inc. (NASDAQ:MSTR), recently advised shareholders to be prepared for a year or two of pain. This warning came after a shareholder, identified as Rob, shared his experience of investing $219,000 in MSTR for his three children. The investment had fallen to $60,000, a decline of over 70%.

Saylor's comments were made during a livestreamed Q&A session on August 17, 2026. He emphasized that shareholders should be patient and understand that the company's stock 'was never designed to behave like a typical equity.' He recommended a holding horizon of seven to ten years, which may be challenging for investors who need the money soon, such as for college tuition.

Strategy Inc.'s second-quarter 2026 filing showed a loss of $24.45 per diluted share, primarily due to an $8.32 billion unrealized loss on digital assets. The company held 846,000 Bitcoin, carried at $49.7 billion against a $63.9 billion cost basis.

In the weeks following Saylor's comments, MSTR has experienced a significant gain, with the stock price rising 35.67% over the past month. However, this increase does not necessarily indicate that Saylor's advice was correct.