Strategy Now Worth Less Than Its Bitcoin Stash — Is Michael Saylor’s ‘Never Sell’ Plan Cracking?

Key Takeaways

Strategy’s market cap has fallen below the value of its Bitcoin reserves.

The inversion has raised questions about the sustainability of Michael Saylor’s “never sell” pledge.

Bitget CEO Gracy Chen says the next major Bitcoin move hinges on interest rate cuts.

Strategy’s market cap has fallen below the value of the Bitcoin it holds, a rare inversion that has raised questions about whether Michael Saylor’s long-standing “never sell” philosophy remains viable.

The move has also prompted discussion over whether the shift could ignite a rebound in Bitcoin’s price, which continues to show a bearish long-term outlook.

On Wednesday, Bitget Chief Executive Gracy Chen highlighted the decline of Strategy on X, stating that its market cap had dropped to approximately $64.4 billion, slipping beneath the estimated $85 billion to $88 billion value of its Bitcoin reserves.

She said the breakdown in the company’s premium over net asset value highlights a structural problem for DAT companies.

“I actually mentioned during my Bloomberg TV interview yesterday that long-tail DATs lack genuine buying interest, but leading DATs like Strategy and Bitmine should still have market appeal,” she wrote.

The Bitget CEO added that the “disappearance of the premium may mark an important moment for the entire DAT industry.”

Across the U.S., trading volumes have thinned dramatically as investors wait for the government to reopen, creating a severe liquidity squeeze, Chen said.

“If market pessimism persists, other DAT firms will face even greater pressure, triggering an industry-wide revaluation,” she warned.

The reversal in Strategy’s valuation has revived debate over whether the company might eventually sell Bitcoin, despite years of insisting it never would.

Since first buying Bitcoin in August 2020, Saylor has positioned the firm’s Bitcoin treasury as much as a philosophical symbol as a financial bet.

After critics raised concerns about the firm’s rising debt last year, Saylor quickly dismissed the risk.

“Bitcoin could go from $100,000 to $1,000,” he said at the time. “The debt is not going to get called; there is no recourse.”

While the firm has long framed Bitcoin as a reserve asset similar to gold, this new market cap–NAV inversion may provide its strongest incentive yet for the firm to consider selling.

Any sale, however, would challenge the company’s identity and risk alienating shareholders.

Nathan Chiron, Chief Revenue Officer at iExec, previously said the psychological weight of a sell-off would have a significant effect on the industry.

“Michael Saylor’s ‘never sell’ ethos has been a core part of the company’s narrative, acting both as a brand identity and a long-term strategic conviction,” Chiron said.

“If Strategy begins to sell, it would not only mark a significant psychological shift for institutional Bitcoin holders but could also introduce near-term volatility and weaken confidence in corporate HODL strategies.”

Strategy’s decreased valuation has raised questions about whether the digital-asset sector is approaching a capitulation point, a phase that in previous cycles has sometimes preceded short-term recoveries in Bitcoin.

However, Chen said Bitcoin’s next decisive move is more likely to be shaped by U.S. monetary policy than company-specific pressures.

“Whether it will start rising or not mainly depends on the progress of U.S. interest rate cuts,” she said in a translated X post, noting that liquidity conditions remain tight as markets await clarity from policymakers.

Chen added that she has recently increased her long exposure, citing what she sees as favorable risk-reward conditions.

She pointed to $97,000 as a key support level, saying she would exit the position if Bitcoin falls below that threshold. Above it, she estimates a potential 50% upside.

“The mindset won’t be too bad as long as I don’t use leverage,” she said.

Even as some speculation grows about a Bitcoin recovery, technical signals point to a less optimistic outlook.

CCN analyst Valdrin Tahiri noted that BTC has carved out a short-term ascending channel, a structure that often supports temporary recoveries.

“Momentum indicators are turning higher,” Tahiri explains, pointing to the RSI pushing above 50 and the MACD crossing into positive territory.

However, he emphasizes that this bounce is far from decisive.

The ascending channel that has formed since Nov. 4 is more characteristic of a corrective structure than an impulsive trend reversal.

“Such channels typically represent corrective movements, not impulsive breakouts,” he wrote.

In Tahiri’s view, the move upward may simply be a pause before another potential leg down.

The post Strategy Now Worth Less Than Its Bitcoin Stash — Is Michael Saylor’s ‘Never Sell’ Plan Cracking? appeared first on ccn.com.

Scroll to Top