Gerber Slams Saylor's Bitcoin Investment Strategy

Veteran investor Ross Gerber has criticized Michael Saylor's strategy of investing in Bitcoin through his firm, Strategy Inc. (NASDAQ:MSTR).

Gerber argues that Strategy's approach of selling MSTR at a high premium to buy 'cheaper' Bitcoin worked during the bull market but now works against them in the bear market.

Saylor is trying to convince people to buy Bitcoin, but Gerber believes he's putting the entire market at risk. He calls Saylor the 'worst thing' to have happened to Bitcoin and says that if its price doesn't move higher, Saylor's strategy will collapse.

Strategy has struggled in 2026, with MSTR stock falling over 12% year-to-date due to unrealized losses when Bitcoin's price fell below the average price at which it was acquired. However, the ongoing rally has eased this situation somewhat, and Strategy resumed its Bitcoin purchases after a two-month buying drought.

MSTR stock is up 40% in a month, but Gerber remains bearish on Bitcoin due to Saylor's actions.