Michael Saylor's Strategy Sells Bitcoin Amid $8.32B Paper Loss, Raising Questions About Crypto Strategy

Strategy, led by Michael Saylor, sold 3,588 Bitcoin for $216 million while facing an $8.32 billion paper loss, prompting skepticism from podcast hosts about the company's pivot from its 'never sell Bitcoin' stance.

Bay Area Metrowire Staff
Business
Michael Saylor's Strategy Sells Bitcoin Amid $8.32B Paper Loss, Raising Questions About Crypto Strategy

In a move that would have been unimaginable a year ago, Michael Saylor's Strategy has sold Bitcoin, according to the latest episode of DH Unplugged. The podcast, hosted by John C. Dvorak and Andrew Horowitz, reported that Strategy sold 3,588 Bitcoin for approximately $216 million while sitting on an $8.32 billion paper loss. The hosts expressed skepticism about the pivot, with Horowitz noting that proceeds from the sale are being used for preferred stock dividends and dollar reserves. "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," Horowitz said.

The episode, titled "He's Selling Bitcoin!" and published July 7, 2026, opened with a wobble across risk assets. The hosts unpacked a soft June jobs print, with a 57,000 payrolls print versus a 110,000 estimate, and April and May revised down by 74,000. They also covered SpaceX's arrival in 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 alongside an 8% share drop.

Dvorak pressed on whether Strategy's structure is "Ponzi-ish," while Horowitz walked through an average purchase price of $75,476 against recent sales between $59,000 and $61,000 per coin. The conversation broadened into the machinery behind the AI trade. The hosts flagged reports that Nvidia's Kyber architecture could slip up to 12 months into 2028, noted Goldman Sachs data showing hedge funds dumped tech hardware and semiconductor exposure for a fourth straight week, and questioned Larry Ellison's sudden speaking tour as Oracle's stock cratered.

Elsewhere, the episode covered 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 was cited pegging alternative unemployment near 25% and inflation around 9%.

Listeners can expect a wide-ranging tour of the tape and the news cycle. The episode is available at dhunplugged.com, via RSS, and on Apple Podcasts, Spotify, and Amazon Music.

Blockchain Registration

QR Code for Blockchain Registration