Early Uber Investor Warns: Stay Away from Saylor’s Strategy, Stick to Pure Bitcoin

Prominent angel investor and early Uber backer Jason Calacanis has taken a strong stance against Michael Saylor’s investment approach and his company Strategy (formerly MicroStrategy). According to him, investors should place their bets on Bitcoin itself, rather than on the complicated structure of Strategy’s stock.

Direct Bitcoin yes, Strategy no In his latest social media post, Calacanis advised investors to stay away from Strategy’s shares. He argued that they are “complicated, layered, and investors lose control over them.” Instead, he believes direct exposure to Bitcoin makes far more sense. This aligns with his previous criticism, where he suggested that Strategy stock should be traded at a discount to its net asset value (NAV).

Aggressive Bitcoin buying harms the brand, says Calacanis Calacanis has also accused Saylor of harming the Bitcoin brand through his aggressive accumulation strategy. He argued that such a concentrated and centralized approach could raise concerns among both investors and regulators. As of now, Strategy holds approximately 638,460 BTC, worth around $74 billion, making it the largest corporate holder of Bitcoin worldwide.

Failure to join the S&P 500 Another setback for Saylor came when Strategy failed to secure entry into the prestigious S&P 500 index. While Saylor claimed the company did not expect to be included in the first quarter of eligibility, JPMorgan analysts called the rejection a “significant failure.” They also suggested this could affect how other index providers view Strategy’s stock. Inclusion in the S&P 500 brings crucial advantages:

🔹 Buying pressure from index funds

🔹 Increased liquidity

🔹 Stronger institutional acceptance For Strategy, such a milestone would not only have boosted market presence but also expanded its reach to a much broader base of institutional investors.

Summary Jason Calacanis has once again made his skeptical stance clear: Bitcoin yes, Strategy no. While Michael Saylor continues his mission of amassing BTC and positioning his company as the ultimate Bitcoin treasury, critics warn that its complex structure and recent failures could serve as a serious red flag for investors.

#bitcoin , #MichaelSaylor , #MicroStrategy , #cryptotrading , #CryptoNews

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