In a move that would have seemed 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, a weekly investing podcast hosted by John C. Dvorak and Andrew Horowitz.
The sale marks a significant pivot for Strategy, which had long been the poster child for corporate Bitcoin accumulation. Horowitz noted that proceeds from the sale are being used for preferred stock dividends and dollar reserves, delivering a sharp 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 news comes amid a broader wobble across risk assets. A soft June jobs print showed 57,000 payrolls versus a 110,000 estimate, with April and May revised down by 74,000. Listeners can expect a wide-ranging tour of the tape and the news cycle, as the hosts unpack SpaceX’s arrival in the NASDAQ 100, which displaces weight from Nvidia, Microsoft and other megacaps; Oracle’s steepest weekly drop since the dot-com bust, with a 19% slide, $130 billion in debt, and $24 billion in negative free cash flow; and renewed strikes on Iran.
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%.
Tesla’s record 480,000 Q2 deliveries alongside an 8% share drop also featured. The hosts do not hide their skepticism about Strategy’s pivot, and the implications are clear: if the largest corporate Bitcoin holder is selling, it could signal a shift in sentiment toward the cryptocurrency as a treasury asset. The sale also raises questions about the sustainability of Strategy’s capital structure and its ability to service debt and dividends. For investors, the episode underscores the importance of questioning narratives and the potential risks in levered plays on volatile assets.
