Michael Saylor's Strategy Sells Bitcoin Amid $8.32B Paper Loss, Sparking Skepticism

Strategy's sale of 3,588 Bitcoin for $216 million, while holding an $8.32 billion paper loss, marks a reversal from its 'never sell' stance and raises questions about its capital structure.

Miami Metrowire Staff
Business
Michael Saylor's Strategy Sells Bitcoin Amid $8.32B Paper Loss, Sparking Skepticism

In a move that would have been unthinkable a year ago, Michael Saylor's Strategy has sold Bitcoin, according to the latest episode of the investing podcast DH Unplugged. The episode, titled "He's Selling Bitcoin!" and hosted by John C. Dvorak and Andrew Horowitz, details how Strategy sold 3,588 Bitcoin for roughly $216 million while sitting on an $8.32 billion paper loss. The proceeds are being used for preferred stock dividends and dollar reserves, a pivot from Saylor's longstanding mantra of never selling Bitcoin.

The hosts express deep skepticism about the decision. Horowitz notes that Saylor, once a Treasury poster child for Bitcoin accumulation, is now selling to serve the capital structure, remarking, "This is the guy that said never sell Bitcoin... Oops." Dvorak presses on whether the structure is "Ponzi-ish," while Horowitz highlights that the average purchase price was $75,476 per coin, compared to recent sales between $59,000 and $61,000. The sale comes amid a broader wobble across risk assets, including a soft June jobs print—57,000 payrolls versus a 110,000 estimate, with April and May revised down by 74,000—and renewed strikes on Iran.

The episode also covers other significant market developments. SpaceX has joined the NASDAQ 100, displacing weight from Nvidia, Microsoft, and other megacaps. Oracle experienced its steepest weekly drop since the dot-com bust, falling 19%, with $130 billion in debt and $24 billion in negative free cash flow. Tesla reported record 480,000 Q2 deliveries but saw an 8% share drop. The hosts question the AI trade, flagging reports that Nvidia's Kyber architecture could slip up to 12 months into 2028, and citing Goldman Sachs data showing hedge funds dumped tech hardware and semiconductor exposure for a fourth straight week.

Additional topics include Microsoft's latest round of roughly 4,800 layoffs pinned on AI, OPEC+ adding 188,000 barrels per day in August, the Strategic Petroleum Reserve falling to 319 million barrels (its lowest since 1983), and a China court handing a death sentence to former Nanjing official Yang Yulin over $325 million in bribes. John Williams's Shadow Stats is cited, pegging alternative unemployment near 25% and inflation around 9%. The episode is available at dhunplugged.com and on major podcast platforms.

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