Tuesday, November 4, 2025

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“Pharma Bro” Martin Shkreli Shorts MicroStrategy, Says Michael Saylor Is “Insane”

Martin Shkreli, the infamous “Pharma Bro” known for his controversial business tactics and stint in federal prison for securities fraud, has entered the Bitcoin conversation with sharp criticism of MicroStrategy (NASDAQ: MSTR) and its co-founder, Michael Saylor. In recent comments, Shkreli labeled Saylor as “insane” for his aggressive Bitcoin strategy, predicting that it will ultimately end in disaster for the enterprise software firm.

Shkreli, whose reputation precedes him as both a provocateur and a divisive figure, disclosed that he is shorting MicroStrategy’s stock—a move that has proven to be both “fun” and “a little painful.” His remarks highlight an emerging debate over whether Saylor’s Bitcoin-heavy corporate strategy is visionary or reckless.

MicroStrategy, under Saylor’s leadership, has become synonymous with institutional Bitcoin adoption. The company, traditionally a business analytics firm, shifted focus dramatically in 2020, using Bitcoin as a treasury reserve asset and issuing debt to fund additional purchases.

As of now, MicroStrategy holds over 152,800 Bitcoin, valued at more than $43 billion. This strategy has not only transformed the company’s identity but has also yielded substantial gains, with its stock price skyrocketing from under $60 in 2020 to over $400 in 2023—a gain exceeding 600%.

Despite this performance, critics like Shkreli argue that such a heavy reliance on Bitcoin is fraught with risk. On his podcast, Shkreli Planet, Shkreli expressed skepticism about the sustainability of MicroStrategy’s approach, claiming, “This has to end poorly, right? I think Saylor’s insane, I think he’s just drunk on [Bitcoin]. This is like a big bubble, and there’s just no way this could end well.”

Saylor has been one of Bitcoin’s most vocal advocates, often pitching it as “digital gold” and a hedge against inflation. His conviction has resonated with some investors, who see MicroStrategy as a proxy for Bitcoin exposure without directly buying the cryptocurrency.

However, Shkreli is far from convinced. He criticized Saylor’s inability to persuade other major corporations, such as Microsoft (NASDAQ: MSFT), to follow suit.

“Saylor is not the best advocate, even though he’s the loudest advocate. I’m starting to turn somewhat bearish on Bitcoin,” Shkreli remarked.

Shkreli’s decision to short MicroStrategy stock suggests he views the company’s Bitcoin-centric strategy as overly speculative. But the pain he describes in holding that short position reflects the stock’s strong performance in recent months, largely fueled by the broader recovery of Bitcoin and crypto markets.

While Shkreli’s criticisms are pointed, they come against the backdrop of MicroStrategy’s undeniable resilience. Despite numerous predictions of its downfall, the company has maintained its strategy, using a mix of equity and debt financing to grow its Bitcoin holdings.

On the other hand, Shkreli’s notoriety stems from inflating the price of life-saving drugs and his legal troubles, which led to a seven-year prison sentence. Since his release in 2022, Shkreli has sought to rebrand himself as a commentator on finance and technology.

His bearish outlook on Bitcoin and MicroStrategy runs counter to the enthusiasm among many retail and institutional investors. Bitcoin has rebounded strongly in 2023, and MicroStrategy’s stock has mirrored that recovery. Nonetheless, Shkreli’s criticism underscores the lingering skepticism about whether Saylor’s strategy is sustainable in the long run.

“Michael Saylor is a fascinating figure,” Shkreli concluded on his podcast. “But I wouldn’t bet my life savings on his dream.”


Information for this briefing was found via Bitcoin News and the sources mentioned. The author has no securities or affiliations related to this organization. Not a recommendation to buy or sell. Always do additional research and consult a professional before purchasing a security. The author holds no licenses.

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