’99>98′: How Michael Saylor Plans to Move Strategy’s Bitcoin Holdings Toward Profit

Michael Saylor is back on everyone’s timelines this Sunday, and as always on the seventh day of the week, he is flirting with the crypto market crowd through a cryptic chart that signals a potential new Bitcoin (BTC) purchase. This time it is a post captioned with the text “99>98,” referencing Strategy’s 98 prior acquisition events, totalling 714,644 BTC as of Feb. 15. 

With Bitcoin trying to find stability near $68,900, below the firm’s $76,056 average cost, a 99th purchase at current levels would lower its blended entry price and, surprisingly, could position the tranche in unrealized profit for the first time since October.

“99>98” move: Is Strategy about to flip its Bitcoin portfolio to profit?

Strategy’s Bitcoin Standard implemented by Saylor back in August 2020 is really all about the numbers, with Bitcoin’s reserve value standing at $50.28 billion right now. The company’s average acquisition price is about $76,056 per BTC, leaving the aggregate position at an unrealized loss of around 7-9% depending on valuation reference. 

A fresh allocation, if one happened this week, would mathematically reduce that average and improve reported performance metrics.

Market structure adds context as Bitcoin is consolidating in the upper $60,000 range. For a treasury vehicle that has accumulated the cryptocurrency for almost 5.5 years, this zone represents a discount not only to recent peaks but also to Strategy’s internal cost basis. A purchase executed here would stand out as one of the few tranches acquired materially below the long-term mean.

On the equity side, Strategy’s enterprise value is near $61 billion, while mNAV ratios indicate the stock trades close to its Bitcoin-adjusted net asset value. That narrows prior premium expansion and reduces dilution sensitivity tied to capital raises for additional BTC acquisitions.

The “99>98” message appears consistent with that cadence. If confirmed, the next transaction would extend Strategy’s Bitcoin holdings beyond 714,644 BTC and demonstrate continued cost averaging during a market phase where spot prices remain under the firm’s historical entry level.