MicroStrategy (MSTR), now rebranded as Strategy Inc., has remade itself from a decades-old business-intelligence software firm into one of the largest corporate holders of Bitcoin. In this episode, we unpack that dramatic pivot — Michael Saylor’s decision to turn the company’s treasury and capital-raising power into an active Bitcoin accumulation vehicle — and how that has transformed the company’s identity and strategy. It’s a tale of two businesses: a legacy analytics software operation that still generates revenue, and a dominant, high-conviction Bitcoin strategy funded by equity and debt issuance. The upside is straightforward: if Bitcoin soars, Strategy Inc. could benefit handsomely from scale and first-mover advantage. The downsides are equally stark: extreme price volatility, accounting quirks, dilution and leverage concerns, and competition from direct Bitcoin products like spot ETFs (plus entrenched rivals in the BI market). Is this a pioneering way to give investors leveraged Bitcoin exposure, or a risky corporate gamble that’s put all the eggs in one highly volatile basket?

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