This article examines MicroStrategy’s unconventional approach to corporate finance—issuing equity and zero-coupon convertible debt and issuing shares to accumulate Bitcoin. Using historical data and expanded Monte Carlo simulations, the authors estimate the probability of Bitcoin’s price declining below critical levels over a typical five- to seven-year debt-maturity window. Results show that the strategy remains solvent except under extreme structural breaks in Bitcoin’s long-term growth. Dilution, rather than insolvency, emerges as the primary equity holder risk. Comparative analysis versus crypto-fund benchmarks demonstrates that MicroStrategy’s stock exhibits the risk-adjusted return profile of a moderately leveraged digital-asset fund. Broader adoption of this model could reshape corporate treasury management, influence monetary policy, and accelerate the integration of digital assets into conventional finance.
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Todd Feldman
San Francisco State University
Chris Yost-Bremm
The Journal of Alternative Investments
San Francisco State University
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Feldman et al. (Wed,) studied this question.
synapsesocial.com/papers/69994b41873532290d01f69c — DOI: https://doi.org/10.3905/jai.2026.1.264