Michael Saylor’s Strategy Sells Bitcoin Amid $8.32 Billion Paper Loss

In a move that would have been unthinkable a year ago, Michael Saylor’s Strategy has sold Bitcoin. According to episode 809 of DH Unplugged, titled ‘He’s Selling Bitcoin!,’ the company sold 3,588 Bitcoin for roughly $216 million while sitting on an $8.32 billion paper loss. The episode, hosted by John C. Dvorak and Andrew Horowitz and published July 7, 2026, opens the second half of the year with a wobble across risk assets.

The hosts unpack the implications of Strategy’s pivot, noting that proceeds from the Bitcoin sale are being used for preferred stock dividends and dollar reserves. Horowitz delivers 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 presses on whether the structure is ‘Ponzi-ish,’ while Horowitz walks through an average purchase price of $75,476 against recent sales between $59,000 and $61,000 per coin.

The broader market context includes a soft June jobs print—57,000 payrolls versus a 110,000 estimate, with April and May revised down by 74,000. SpaceX’s arrival in the NASDAQ 100 displaces weight from Nvidia, Microsoft, and other megacaps. Oracle’s steepest weekly drop since the dot-com bust, with $130 billion in debt and $24 billion in negative free cash flow, raises questions about the AI trade. Tesla’s record 480,000 Q2 deliveries accompany an 8% share drop.

The conversation broadens into the machinery behind the AI trade. The hosts flag reports that Nvidia’s Kyber architecture could slip up to 12 months into 2028, note Goldman Sachs data showing hedge funds dumped tech hardware and semiconductor exposure for a fourth straight week, and question Larry Ellison’s sudden speaking tour as Oracle’s stock cratered. Elsewhere they cover 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 find the full discussion at dhunplugged.com or on Apple Podcasts, Spotify, and Amazon Music. Episode 809 is available now wherever podcasts are heard.

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