Michael Saylor's Strategy Sells Bitcoin Amid $8.32 Billion Paper Loss, Raising Skepticism on Crypto Strategy

Strategy, led by Michael Saylor, sold 3,588 Bitcoin for $216 million while facing an $8.32 billion paper loss, signaling a major pivot that has drawn skepticism from market commentators.

Phoenix Metrowire Staff
Business
Michael Saylor's Strategy Sells Bitcoin Amid $8.32 Billion Paper Loss, Raising Skepticism on Crypto Strategy

In a move that would have been unthinkable a year ago, Michael Saylor's Strategy has sold Bitcoin. The company offloaded 3,588 Bitcoin for roughly $216 million while sitting on an $8.32 billion paper loss, according to the latest episode of DH Unplugged, titled "He's Selling Bitcoin!" hosted by John C. Dvorak and Andrew Horowitz. The sale marks a dramatic reversal for Saylor, who had long been the most prominent corporate advocate for holding Bitcoin as a treasury asset.

Proceeds from the sale are being used for preferred stock dividends and dollar reserves, a decision that drew sharp criticism from the hosts. Horowitz noted, "This is the guy that said never sell Bitcoin. He was a Treasury poster child, is now selling to serve as the capital structure. Oops." Dvorak questioned whether the capital structure could be described as "Ponzi-ish," while Horowitz highlighted that Strategy's average purchase price was $75,476 per Bitcoin, contrasting with recent sales prices between $59,000 and $61,000 per coin.

The broader market context includes a soft June jobs report showing 57,000 payrolls added versus a 110,000 estimate, with April and May revised down by 74,000. SpaceX 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. The hosts also discussed Tesla's record 480,000 Q2 deliveries alongside an 8% share drop.

The episode delved into the machinery behind the AI trade, flagging reports that Nvidia's Kyber architecture could slip up to 12 months into 2028. Goldman Sachs data showed hedge funds dumping tech hardware and semiconductor exposure for a fourth straight week. The hosts questioned Larry Ellison's sudden speaking tour as Oracle's stock cratered. Other topics included Microsoft's latest round of roughly 4,800 layoffs tied to 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 was cited, pegging alternative unemployment near 25% and inflation around 9%.

The hosts expressed skepticism about the sustainability of the AI trade and the broader market rally, given the weakening labor market and geopolitical tensions, including renewed strikes on Iran. The episode, available at dhunplugged.com, offers a wide-ranging tour of the tape and the news cycle for investors seeking the story behind the tape.

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