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

Strategy, led by Michael Saylor, sold 3,588 Bitcoin for ~$216 million while facing an $8.32 billion paper loss, prompting criticism from DH Unplugged hosts who highlight the contradiction with Saylor's previous 'never sell' stance.

DC Metrowire Staff
Business
Michael Saylor's Strategy Sells Bitcoin Amid $8.32B Paper Loss, Sparking Skepticism from Podcast Hosts

In a move that would have been unthinkable a year ago, Michael Saylor's Strategy has sold Bitcoin. The company sold 3,588 Bitcoin for roughly $216 million while sitting on an $8.32 billion paper loss, according to the latest episode of DH Unplugged, a weekly investing podcast hosted by John C. Dvorak and Andrew Horowitz.

The hosts expressed skepticism about the pivot. Horowitz noted that proceeds from the Bitcoin sale are being used for preferred stock dividends and dollar reserves, then delivered a pointed critique: "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 pressed on whether the 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 episode, titled "He's Selling Bitcoin!" and published July 7, 2026, opened the second half of the year with a wobble across risk assets. Beyond the Bitcoin sale, the hosts covered a soft June jobs print, with 57,000 payrolls versus a 110,000 estimate, and April and May revised down by 74,000. SpaceX joined the NASDAQ 100, displacing weight from Nvidia, Microsoft and other megacaps. Oracle suffered its steepest weekly drop since the dot-com bust, sliding 19% with $130 billion in debt and $24 billion in negative free cash flow. Tesla posted record 480,000 Q2 deliveries alongside an 8% share drop.

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 they 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 is 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 hosts blend Federal Reserve watching, earnings analysis, commodity moves and offbeat cultural observation for investors who want the story behind the tape. Episode 809 is available now wherever podcasts are heard.

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