According to CoinWorld news, MicroStrategy (MSTR) stock price premium has decoupled from its historical Bitcoin performance for the first time. These changes come amid increased proxy trading of Bitcoin (BTC), with MicroStrategy now being a pioneer and the largest corporate holder of the leading cryptocurrency. The decoupling of MicroStrategy's premium from Bitcoin has raised questions about the sustainability of Michael Saylor's financial model. Other concerns include whether new entrants into the Digital Asset Treasury (DAT) market are undermining the company's unique role as Wall Street's gateway to Bitcoin. In hindsight, MicroStrategy's ability to accumulate Bitcoin on a large scale has relied on a simple reflexive mechanism. When its stock trades above its net asset value (mNAV), it can issue shares, raise cash, and acquire BTC at a premium. Since 2020, this financial alchemy has been the cornerstone of Saylor's strategy. However, according to researcher Joseph Ayoub, the emergence of multiple DATs is weakening this flywheel effect. If true, this would mark a decisive turning point, as MicroStrategy's ability to fund new Bitcoin purchases through equity issuance may be permanently impaired. DATs are equity companies that sell stock to purchase digital assets. Since 2020, the digital asset treasury model has surged from around $10 billion in NAV to over $100 billion. In contrast, Bitcoin ETFs (exchange-traded funds) currently stand at about $150 billion. DATs attract investors because they offer equity exposure to crypto assets, often at a high premium. Ayoub describes them as modern closed-end funds. Unlike ETFs, most DATs cannot redeem shares for the underlying assets. This makes valuations related to market sentiment rather than a direct redemption mechanism. This dynamic is reminiscent of the Grayscale Bitcoin Trust (GBTC), which traded at a hefty premium before plummeting to a 50% discount during the 2022 bear market. Nic Carter from Castle Island Ventures pointed out historical similarities. He cited an article from Be Water that compares today's DAT boom to the investment trust craze of the 1920s, listing many parallels. The risks facing Saylor's MicroStrategy are increasing, with a decline in premiums coinciding with growing scrutiny of Saylor's concentrated exposure to Bitcoin. As previously reported by BeInCrypto, some investors believe the company's recent updates have amplified Bitcoin's volatility. This would make the risks faced by stockholders more akin to leveraged ETFs rather than traditional software companies. If MSTR continues to trade at a discount, there could be repercussions. Shareholder lawsuits may demand redemptions at prices closer to NAV. Regulators may reclassify MicroStrategy as an investment company by referencing precedents like Tonopah Mining from the 1940s and the GBTC saga of 2021. Such a move would impose stricter rules or force structural changes. In this context, Ayoub warns that equity-funded Bitcoin treasuries are approaching a saturation point. Bitcoin treasury data shows that MicroStrategy holds nearly 630,000 BTC, with manageable debt levels. However, its decoupling from premiums might indicate that its once-virtuous cycle is collapsing. If so, this company, which transformed corporate Bitcoin strategy into financial alchemy, may face erosion from its unique advantages rather than the most severe tests presented by a bear market.

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