Early Uber Investor on Saylor's Strategy: 'I Would Never Touch It'

In a recent social media post, prominent venture capitalist Jason Calacanis has stated that he would never touch Michael Saylor's Strategy even if the stock were to crash. 

Calacanis also argues that there should be no Bitcoin bailouts if the company happens to go underwater. 

The caustic comments of the early Uber investor come after the Wall Street Journal reported that digital asset treasury companies are "crumbling." 

Earlier, Calacanis argued that investors have to avoid Saylor and buy Bitcoin directly. Back then, the angel investor said that he was 95% certain that he would end up being right. 

He has also claimed that Strategy's bet was too "convoluted," but he has stopped short of describing it as a Ponzi scheme in his most recent social media post. 

"Whenever you see a company using creative new metrics or innovative capital structures, consider that worthy of deeper investigation. Could be nothing, could be brilliant, or could be something bad," Calacanis said back in April.

For now, there is only a 3% chance of Strategy being forced to liquidate its holdings. 

Will Strategy bounce back?

As reported by U.Today, Jim Chanos, founder of Kynikos Associates, recently announced that the firm had unwound its anti-MSTR trade after pocketing hefty returns. The stock of the leading Bitcoin treasury firm had crashed by a whopping 45% after Chanos initially announced his bet against Saylor in mid-May. 

In late October, Strategy had to boost yield on its preferred shares in order to increase faltering demand. 

Some believe that Chanos's latest move might be a sign that cryptocurrency treasury companies will finally see some sort of bullish reversal after facing steep losses. 

For now, however, they remain under rather severe pressure, and those companies whose crypto holdings are currently in the red will struggle to sell more shares.