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Early Uber Investor: Avoid Saylor, Buy Bitcoin Directly

On September 26, 2025 by voice

Prominent Uber investor Jason Calacanis has reiterated that investors who want to get exposure to Bitcoin should buy the leading cryptocurrency directly instead of buying the shares of Strategy (MSTR).

Calacanis, who has emerged as one of the most vocal Strategy bears, believed there is a 75% chance that he will end up being correct.

As reported by U.Today, Saylor recently stated that investors should stay away from Saylor “as far as possible.”

Strategy’s recent plunge

The shares of the biggest Bitcoin corporate treasury holder, which boasts a total of 639,835 coins, have now plunged by 35% from their local peak of $457.

Strategy critics, including famed short seller James Chanos, have long argued that the company does not deserve to trade at a significant premium to net asset value (NAV).

Moreover, the company recently issued a new equity issuance policy, which will negatively affect its ability to buy Bitcoin in the future.

Of course, the company also took a big hit in early September after it got snubbed by the S&P 500. Even though Saylor tried to downplay the severity of the decision, JPMorgan predicted that this could negatively affect Strategy as well as other Bitcoin treasury firms.

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