Michael Saylor’s NAV-Backed Bitcoin Strategy Faces Heat as Analysts Predict Sharp BTC Correction

MicroStrategy’s billion-dollar bitcoin gamble hits turbulence as Wall Street sounds the alarm.

The NAV Tightrope Walk

Saylor’s leveraged bitcoin acquisition spree—funded through equity offerings and convertible debt—now faces scrutiny as BTC wobbles near key support levels. The company’s stock (MSTR) trades at a staggering 175% premium to its net asset value, a disconnect that’s raising eyebrows even among crypto true believers.

Analysts Ring the Warning Bell

JPMorgan strategists note MicroStrategy’s 214,000 BTC stash could trigger margin calls if prices dip below $50,000—a scenario that would make corporate treasury’s favorite ‘inflation hedge’ look more like a leveraged short on common sense. Meanwhile, crypto VC firms quietly accumulate puts while publicly tweeting diamond hands.

The Institutional Paradox

While Saylor’s ‘bitcoin-as-corporate-NAV’ playbook inspired dozens of imitators, the strategy now faces its first real stress test. As one hedge fund manager quipped: ‘Turns out volatility matters when you’re using shareholder capital to play crypto roulette.’ The coming weeks will reveal whether this is a buying opportunity—or the moment crypto’s Wall Street embrace goes full Icarus.

Strategy class A shares drop could cause Bitcoin and crypto market slump

According to market watchers, the fall in Strategy’s NAV could mean investors are worried about its shares’ dilution, leverage and the structure of the company’s Bitcoin-heavy balance sheet. The company frequently issues stock to acquire more BTC, a business plan that leans on the shares trading at a premium to the Bitcoin the firm buys.

Dom Kwok, co-founder of blockchain education app developer EasyA, said Strategy’s business model is sensitive to how the market values the company relative to its holdings. According to him, no corporate treasury with substantial BTC reserves has ever traded below its net asset value for long without facing pressure on its strategy.

very important week coming up for $MSTR (and markets overall). @MicroStrategy is currently trading below NAV (ie its market cap is lower than the value of its $BTC holdings).

no treasury company has ever traded below its NAV for an extended period of time.

the model only…

— Dom Kwok | EasyA (@dom_kwok) November 16, 2025

Kwok noted that Strategy’s approach functions only when its market-to-NAV ratio stays above 1. A premium gives the firm an incentive to issue new shares to acquire more Bitcoin without meaningfully reducing existing shareholders’ exposure, and once the shares trade at a discount, that calculus flips over. 

“Strategy gives away more ownership through its undervalued shares than it receives in return, via bitcoin. If MSTR stock continues to decline, expect volatility across the market,” Kwom surmised, insisting the class A stock performance will determine investor confidence in BTC.

Arca executive disputes chatter of BTC forced selling

Jeff Dorman, chief investment officer at digital assets firm Arca, says there are persistent misconceptions about the Strategy’s financial structure and its impact on Bitcoin markets. In a lengthy post on X late Sunday, Dorman disputed theories about the firm selling part of its massive Bitcoin holdings, mostly based on misunderstandings about corporate debt, equity and governance.

“It takes

Per Dorman, crypto exchange-traded funds (ETFs) are far more significant marginal buyers and could likely influence the market more than any single corporate treasury.

Dorman also dismissed the idea that Strategy could face an activist campaign to force sales of its BTC holdings, noting that Saylor controls roughly 42% of voting power. He said the firm’s debt carries no covenants requiring liquidations and its Core software business generates positive cash flow, keeping interest obligations manageable. 

“Interest expense is low and manageable – don’t forget the CORE tech business still has positive cash flow. No one ever defaults because of debt maturities. Investors are sheep and will almost always roll the debt (extend and pretend). If you follow anyone saying MSTR is a risk to BTC, tell them to call me,” he concluded.

Bitcoin fear-greed sentiment collapses to 10

Strategy’s discount to NAV surfaced during Bitcoin’s Fear and Greed Index slump to 10 on Monday, its lowest reading since the market crash triggered by the COVID-19 outbreak in 2020.

Price charts show Bitcoin retesting a breakdown level NEAR $95,500, where sellers continue to reject upward attempts. As long as the price stays below that band, more declines toward the $93,200 to $92,200 region are more likely to happen. 

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