Calacanis says $MSTR is complicated, advises buying BTC directly
Early Uber investor Jason Calacanis said on X that if you want exposure to Bitcoin, just buy BTC and “stay as far away from $MSTR as possible,” calling the stock complicated and layered.
He weighed in on the perennial “own BTC vs own $MSTR” debate. In a post on Sept. 12, Calacanis wrote that the simplest path is to buy Bitcoin directly and to avoid Strategy’s stock ($MSTR) because it’s “complicated, layered and you lose control.” However, the investor added a light disclaimer not to take financial advice from a podcaster/angel investor.
Earlier this year, Calacanis argued that $MSTR should trade at a discount to its Bitcoin holdings, given the company’s debt and the fact that shareholders don’t hold keys. He also criticized Michael Saylor’s accumulation strategy as harmful to Bitcoin’s image, saying large, aggressive corporate buys risk “breaking the game.”
For some crypto investors, his view resonates because owning BTC allows self-custody (if chosen) and direct price exposure. Owning $MSTR adds corporate leverage, governance and valuation variables (the shares can trade at a premium or discount to the underlying BTC), plus idiosyncratic catalysts like index inclusion.
Strategy (the rebranded MicroStrategy) reports around 638,460 BTC on its balance sheet (about $74 billion at recent prices). The company missed inclusion in the S&P 500 in its first eligible window; JPMorgan analysts called the snub a setback that could affect how index providers view $MSTR and similar names. Index addition typically brings index‑fund demand, deeper liquidity and a broader investor base.
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