MSTR Stock Up 40% in a Month, but Ross Gerber Still Calls Michael Saylor the ‘Worst Thing’ to Happen to B

Veteran investor Ross Gerber accused Michael Saylorof putting the entire Bitcoin(CRYPTO: BTC) market at risk through the approach taken by his firm, Strategy Inc.(NASDAQ:MSTR).

Gerber Slams Saylor’s Playbook

In an exclusive chat with Benzinga, Gerber said Strategy’s tactic of selling MSTR at a high premium to buy “cheaper” Bitcoin worked in the bull market but started to “unwind” in the bear market.

“So now he’s [Saylor] created a reverse situation. What was working for him all those years now works against him,” the CEO of Gerber Kawasaki Wealth and Investment Management argued.

Strategy shares have historically traded at a premium, meaning the stock price values the company higher than the BTC on its balance sheet. However, when the stock trades at a discount, the company’s ability to raise capital by selling new shares slows down, since it becomes dilutive.

This is exactly what happened in recent months. Strategy paused Bitcoin buying entirely and focused on cleaning up its balance sheet. It even offloaded some of its BTC to bolster its dollar reserves.

Saylor the ‘Worst Thing’ to Happen to Bitcoin, Says Gerber

Gerber said that Saylor is “trying very hard” to convince people to buy Bitcoin.

‘If Bitcoin doesn’t reverse its price movement and move higher, he’s [Saylor] dead. It’s just a matter of time till that entire thing collapses,” the Teslainvestor added.

Gerber added that Saylor’s Strategy has put the entire market at risk, going so far as to call the Bitcoin bull the “worst thing” to have happened to the cryptocurrency.

He also voiced deep frustration with Saylor’s AI-generated videos on X, saying that nothing makes him more bearish on Bitcoin than watching Saylor punching out bears.

Strategy didn’t immediately return Benzinga’s request for comment.

Are Things Changing For the Better?

Strategy, the world’s largest Bitcoin corporate holder, has struggled in 2026, with its common stock falling more than 12% year to date.

The firm recorded unrealized losses when Bitcoin’s price fell below the average price at which it was acquired.

However, the ongoing rally has eased the situation somewhat. Strategy’s Bitcoin stash is back to showing paper profits, and MSTR stock is up 40% in a month. The company also resumed its Bitcoin purchases, ending a two-month buying drought.

Saylor had earlier advised investors to take a long-term approach to Bitcoin and refrain from investing unless they plan to hold it for at least four years.

Price Action: At the time of writing, BTC was seen trading at $79,051.04, up 1.32% over the last 24 hours, according to data from Benzinga Pro.

Strategy shares fell 1.15% in after-hours trading. The stock closed 4.42% higher at $132.94 during Monday’s regular trading session.

According to Benzinga’s Edge Stock Rankings, MSTR stock has lagged on a long-term basis but has exhibited robust short- and medium- term price trends.

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