Bitcoin News Today: Investors Revolt as Saylor’s Bitcoin Premium Strategy Unravels

Michael Saylor’s Bitcoin treasury strategy, which has long positioned Strategy Inc. (formerly MicroStrategy) as a market bellwether for crypto sentiment, is currently facing a significant downturn. Shares of the company have declined by 15% this month, eroding much of the premium that once distinguished the stock from its underlying Bitcoin holdings. The company’s market multiple—referred to as mNAV—has dropped to 1.57, far below earlier levels and signaling a shift in investor sentiment. This decline is particularly notable given the broader crypto market remains in a bull phase, raising concerns about the sustainability of the corporate-treasury model that Saylor pioneered [1].

At the heart of the issue is Strategy’s evolving financing strategy. The company recently attempted to raise capital through a new preferred stock offering, but it only secured $47 million, far below Saylor’s target. To address the shortfall, the company has turned back to issuing common shares, despite previous commitments to limit dilution. This reversal has prompted investor backlash, with many viewing it as a breach of trust. The market is now beginning to react to the perceived inconsistency in corporate strategy, with some analysts warning of a potential negative flywheel effect—where declining share price undermines the company’s ability to acquire Bitcoin, leading to further premium erosion [1].

Saylor’s corporate-treasury model—raising equity and debt to purchase Bitcoin, then leveraging the market’s willingness to assign a premium to its holdings—has inspired a wave of similar companies. According to BitcoinTreasuries.net, these firms now collectively hold over $108 billion in Bitcoin, accounting for nearly 5% of the total supply. The model’s influence has extended beyond Strategy, with numerous smaller firms adopting similar strategies. However, these firms often lack the scale, liquidity, and creditworthiness of Strategy, making them more vulnerable to market corrections. As Jake Ostrovskis of Wintermute’s OTC Desk noted, the decline in Strategy’s premium is a natural response to increased competition and the availability of alternative investment vehicles [1].

One such alternative is the emergence of spot Bitcoin ETFs, which offer investors direct exposure without the risks of corporate governance, leverage, or dilution. These funds have gained traction, particularly among institutional investors, and are now competing more directly with corporate-treasury vehicles. Furthermore, investor interest is shifting toward alternative cryptocurrencies like Ether and Solana, which are seen as more suited to decentralized finance applications. Ether-focused treasuries alone have already committed more than $19 billion to digital assets, further fragmenting the investment landscape [1].

The broader implications of the market shift are significant. Capriole Investments has noted that nearly one-third of publicly traded companies with Bitcoin on their balance sheets now trade below the value of those reserves, highlighting the growing pressure on the corporate-treasury model. Smaller firms, in particular, face challenges related to limited liquidity and reliance on convertible notes, which increase interest burdens and maturity risks. Strategy has previously stated its intention to retire all convertible notes within four years, but many of its smaller counterparts lack the financial engineering capacity to replicate this approach [1].

In the face of mounting skepticism, Saylor has dismissed the criticism, recently posting an AI-generated image of himself walking past a giant bear. The company has not responded to requests for comment, but his supporters argue that maintaining flexibility could prove beneficial if Strategy gains inclusion in the S&P 500 or if Bitcoin experiences another boom. However, as Charles Edwards of Capriole Investments has warned, a 50% drop in Bitcoin’s price could trigger widespread questioning of the corporate-treasury strategy, particularly among firms that bought in at higher valuations [1].

Source: [1] Michael Saylor hit by market revolt as his Bitcoin premium sinks (https://fortune.com/crypto/2025/08/28/michael-saylor-strategy-microstrategy-bitcoin-premium-sinks/) [2] Michael Saylor Hit by Market Revolt as His Bitcoin Premium ... (https://finance.yahoo.com/news/michael-saylor-hit-market-revolt-130000575.html) [3] The MicroStrategy-Style Treasury Strategy: Why It Works ... (https://www.joannix.org/post/the-microstrategy-style-treasury-strategy-why-it-works-and-how-to-value-it)