Veteran investor Ross Gerber has launched a sharp attack on Michael Saylor, accusing him of putting the entire Bitcoin (CRYPTO: BTC) market at serious risk.
Gerber, the CEO of Gerber Kawasaki Wealth and Investment Management, made the remarks in an exclusive interview with Benzinga, targeting the strategy employed by Saylor’s firm, Strategy Inc. (NASDAQ: MSTR).
Gerber argued that Strategy’s approach of selling MSTR shares at a high premium to purchase “cheaper” Bitcoin worked well during bull market conditions but began to “unwind” once sentiment turned negative.
“So now he’s [Saylor] created a reverse situation. What was working for him all those years now works against him,” Gerber said during the interview.
Strategy shares have historically traded at a premium to the value of the Bitcoin held on its balance sheet, giving the company significant capacity to raise fresh capital through new share issuances.
When the stock trades at a discount to its Bitcoin holdings, however, issuing new shares becomes dilutive, undermining the firm’s ability to continue accumulating the cryptocurrency.
That dynamic played out in recent months, forcing Strategy to pause Bitcoin purchases entirely while it focused on stabilizing its balance sheet, even selling some of its BTC holdings to rebuild dollar reserves.
Gerber went further, stating that if Bitcoin fails to reverse its price movement and trend higher, Saylor’s entire operation faces an existential threat, warning “it’s just a matter of time till that entire thing collapses.”
The veteran investor also expressed frustration with Saylor’s AI-generated videos posted on X, stating that nothing makes him more bearish on Bitcoin than watching that content.
Gerber went so far as to call Saylor the “worst thing” to have happened to Bitcoin, citing the systemic risk that Strategy’s leveraged accumulation model poses to the broader cryptocurrency market.
Strategy, recognized as the world’s largest corporate holder of Bitcoin, has struggled through 2026, with its common stock down more than 12% year to date before the recent recovery.
The firm recorded significant unrealized losses during the period when Bitcoin’s price fell below the average acquisition cost of its holdings.
The recent market rally has provided some relief, with Strategy’s Bitcoin treasury returning to paper profits and MSTR stock surging approximately 40% over the past month.
The company also resumed Bitcoin purchases, ending a two-month buying hiatus, while Saylor has continued to publicly urge investors to take a long-term view and avoid investing unless they plan to hold for at least four years.
At the time of reporting, MSTR shares closed 4.42% higher at $132.94 during regular trading, before slipping 1.15% in after-hours trade, while Bitcoin was changing hands at $79,051.04, up 1.32% over the prior 24 hours.
