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MicroStrategy Investors Told to Ride Through Two Years of Pain

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A father who had invested $219,000 in MicroStrategy (MSTR) for his three children saw his investment drop to $60,000, sparking a question from the investor to CEO Michael Saylor during a Q&A session on August 17, 2026. The investor, identified as Rob, said his position had fallen by over 70%. Saylor responded by advising shareholders to be prepared for a 'difficult year or two' before seeing returns. He also stated that investors should have a four-year holding horizon, ideally seven to ten years.

Saylor's comments came after the company's second-quarter 2026 filing showed a loss of $24.45 per diluted share, mainly due to an $8.32 billion unrealized loss on digital assets. The company holds 846,000 bitcoin, carried at $49.7B against a $63.9B cost basis.

Since Saylor's comments, the stock has seen a significant gain, up 35.67% in the past month, but still sits far below its year-ago price.

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