Michael Saylor, executive chairman of Strategy (formerly MicroStrategy), admitted that the company's $8.5 billion STRC perpetual preferred stock was designed with the help of OpenAI's ChatGPT. The revelation came as STRC's price slipped below its $100 par value, trading as low as $86—a 14% discount that has investors questioning the stability of the so-called 'Bitcoin buying flywheel.'
ChatGPT Gave the Green Light, Saylor 'Couldn't Think of It'
According to a post on X by user @_FORAB and a report from Crypto Briefing, Saylor shared a clip where he said he never could have come up with the structure himself. When he asked ChatGPT, the AI replied that while no one had ever done such a thing before, it was fully compliant. Launched in July 2025, STRC is a perpetual preferred stock with no maturity, paying high dividends. It currently offers an annualized yield of 11.5%, and the company is considering semi-monthly payments to attract income-seeking investors. In liquidation, STRC holders have priority claims.
How It Works: No BTC Collateral, Direct Coin Buying
The brilliance of the mechanism is that capital raised does not require Bitcoin as collateral but is instead used to purchase more Bitcoin. Investors earn yield while the company continuously accumulates Bitcoin reserves without adding debt risk. This model has been dubbed the 'strongest financing flywheel ever' by the crypto community. Saylor previously noted STRC's Sharpe ratio exceeded 3, indicating strong risk-adjusted returns.
Price Drop to $86 Sparks Sell-Off Fears
But the flywheel is showing cracks. STRC slid from its $100 par to as low as $86, a 14% discount. For a perpetual preferred stock, trading below par signals waning investor confidence. Saylor has said he would consider share buybacks or dividend adjustments to support the price, but the market remains skeptical. Many speculate that if the discount worsens, the company might be forced to trigger a mechanism to pull the price back to $100—potentially requiring a sale of its Bitcoin hoard. Analysts warn that Strategy's entire model depends on Bitcoin's long-term appreciation. In a prolonged bear market, sustaining $8.5 billion in high dividend payouts would be extremely challenging—a reality ChatGPT could not fully simulate in its original design.