This time, angel investor Jason Calacanis is urging investors to steer clear of Michael Saylor’s Strategy (formerly MicroStrategy), arguing that the stock adds layers of complexity without offering real advantages over simply owning Bitcoin directly.

In a recent post, Calacanis described Strategy’s structure as “complicated” and warned that investors “lose control” by holding its shares. His comments continue a long-running feud with the world’s largest Bitcoin treasury firm. Earlier this year, he argued that the company’s stock should trade at a discount to its net asset value (NAV), given its dependence on Bitcoin’s price and limited operational diversity.

A Corporate Giant Built on Bitcoin

Strategy currently holds around 638,460 BTC, worth approximately $74 billion at current market prices. Saylor has positioned the company as a hybrid — part software firm, part corporate Bitcoin ETF — allowing equity investors to gain indirect exposure to the cryptocurrency. Supporters say the strategy has given Wall Street a bridge to Bitcoin that bypasses regulatory obstacles. Critics counter that it concentrates risk and ties the stock’s fate almost entirely to crypto’s volatility.

S&P 500 Snub Sparks Debate

The company’s profile suffered a blow earlier this month when it failed to make the cut for the S&P 500 index. While Saylor insisted that inclusion was never expected on the first try, JPMorgan analysts called the rejection a “major setback.” The bank warned that the decision could influence other index providers, limiting Strategy’s appeal to traditional funds.

S&P 500 membership is often seen as a game-changer: it forces passive index funds to buy shares, boosts liquidity, and dramatically broadens institutional exposure. Without that tailwind, Strategy must rely more heavily on its Bitcoin narrative to attract investors.

The Bigger Question: Stock or Bitcoin?

For Calacanis, the takeaway is straightforward — why buy stock in a company that’s essentially a wrapper around Bitcoin when you can own the asset directly? His view reflects a broader skepticism on Wall Street about whether crypto should be pursued through equities, ETFs, or direct holdings.

Even so, Strategy’s rise under Saylor has been remarkable, transforming it from a mid-sized software company into a lightning rod for the future of corporate treasury management. Whether its gamble proves visionary or reckless remains a question that only time — and Bitcoin’s price — will answer.

The information provided in this article is for educational purposes only and does not constitute financial, investment, or trading advice. Coindoo.com does not endorse or recommend any specific investment strategy or cryptocurrency. Always conduct your own research and consult with a licensed financial advisor before making any investment decisions.

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