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Strategy's Bitcoin Rollercoaster Investors

Wall Street Journal Markets •
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Despite a nearly 40% slide in shares of Michael Saylor’s bitcoin-hoarding company, Strategy, this year, some fervent believers remain undeterred. Investor James Anderson, for example, doubled down on his positions during a summer free fall, embracing a "buy when there's blood in the streets" mentality, even if it meant his own.

Anderson, 37, is part of a dedicated fan base sticking with Strategy through bitcoin's steep declines. Some are drawn to the potential for amplified bitcoin gains or dividends from Strategy's preferred shares, while others hold a deep-seated belief in bitcoin's long-term resurgence. Strategy, founded by Michael Saylor in 1989, has pivoted from software to become a major bitcoin holder, inspiring similar companies.

However, bitcoin's selloff has prompted Strategy to reassure investors. In a recent turnaround plan, the company announced stock buybacks and the sale of some bitcoin, a move contrary to Saylor's previous advice. While Strategy's common stock and its dividend-paying preferred stock, Stretch, have seen some recovery since the plan's unveiling, they remain significantly below their record highs. Nonetheless, some Strategy enthusiasts maintain faith in Saylor's ability to steer the company back to stability.