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Michael Saylor Hints at New Strategy Shift as Bitcoin Community Speculates

Michael Saylor Hints at New Strategy Shift as Bitcoin Community Speculates. Source: Gage Skidmore from Surprise, AZ, United States of America, CC BY-SA 2.0, via Wikimedia Commons

For more than a year, MicroStrategy Executive Chairman Michael Saylor has stuck to a familiar routine: posting a chart of orange dots almost every Sunday on X, teasing the possibility of another Monday bitcoin (BTC) purchase. This weekend, however, he broke the pattern—sharing the same chart but adding the cryptic line, “what if we start adding green dots.”

The subtle change immediately sparked debate across the bitcoin community. Many observers believe the green dots could signal a shift in MicroStrategy’s capital strategy, potentially hinting at stock buybacks, adjustments to the balance sheet, or even—more controversially—the possibility of future bitcoin sales.

Speculation intensified after CEO Phong Le, speaking on a recent podcast, clarified that MicroStrategy faces no near-term refinancing risk. He explained that the company might consider selling bitcoin only if its market multiple to net asset value (mNAV) drops below 1, enabling it to fund dividends tied to its perpetual preferred equity. Le also noted that MicroStrategy could strategically sell higher cost-basis bitcoin to offset capital gains, a move that could ultimately increase bitcoin per share despite reducing raw holdings.

Any discussion of selling BTC is significant given Saylor's long-held mantra: “You do not sell your Bitcoin.” Yet MicroStrategy’s current challenges are hard to ignore. The company—the largest publicly traded corporate holder of bitcoin with nearly 650,000 BTC—has seen its stock price fall sharply, down 41% year-to-date and roughly 70% from its peak last year.

This downturn has limited its ability to raise capital through common stock offerings, pushing MicroStrategy toward preferred share issuances to maintain its bitcoin-buying strategy. Critics argue that sustaining preferred dividends without diluting common shareholders or selling BTC will become increasingly difficult unless market conditions improve.

With Saylor hinting at a potential evolution in strategy, the crypto world is now watching closely to see whether those green dots signal a new chapter for MicroStrategy—and for corporate bitcoin adoption.

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Great article. Requesting a follow-up. Excellent analysis.

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Great article. Requesting a follow-up. Excellent analysis.
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