Analyst Says Strategy Won’t Need to Sell Bitcoin in Next Bear Market
Crypto analyst Willy Woo argues that Michael Saylor’s company Strategy will not be forced to sell its Bitcoin holdings even during a prolonged market downturn, citing the firm’s flexible debt structure and cash management strategy.
Strategy’s strong financial position
Woo explained that Strategy’s liabilities consist primarily of convertible senior notes — a form of debt that can be repaid in cash, common stock, or a mix of both. This structure gives the company freedom to avoid selling its Bitcoin reserves when market conditions deteriorate.
According to Woo, only an “insanely long and deep bear market” could compel the firm to liquidate any portion of its assets. “Liquidation of MSTR next bear market? Doubt it,” he wrote on social media, referring to Strategy’s ticker symbol on Nasdaq.
Michael Saylor’s Bitcoin conviction
Under executive chairman Michael Saylor, Strategy has become the largest publicly traded corporate holder of Bitcoin, with over 226,000 BTC as of October 2025. The company’s aggressive accumulation strategy — financed through a mix of bond sales and equity offerings — has turned it into a bellwether for institutional Bitcoin exposure.
Saylor has repeatedly stated that Bitcoin represents “digital energy” and “the most reliable long-term store of value,” dismissing concerns about volatility or short-term market cycles.
Convertible bonds and repayment options
Convertible senior notes provide flexibility uncommon in traditional corporate debt. As each tranche reaches maturity, Strategy can either redeem it with cash or allow conversion into stock, depending on market conditions.
This means that even in a severe bear market, the company could opt to issue new shares or use cash reserves rather than selling Bitcoin to service its debt. Analysts view this structure as a strategic buffer that shields Strategy from forced liquidations that often plague over-leveraged crypto firms.
Analyst sentiment and broader implications
Willy Woo’s remarks underscore growing investor confidence in Strategy’s balance sheet. Unlike miners or leveraged funds that depend on high Bitcoin prices to maintain solvency, Strategy operates more like a long-term treasury holding digital assets as collateral.
Woo’s analysis suggests that the company’s fundamentals make it one of the most resilient institutional players in the Bitcoin ecosystem — capable of weathering even a multi-year downturn without offloading its reserves.
Outlook
With Bitcoin’s price still consolidating below its previous all-time highs, Strategy’s accumulation strategy remains under scrutiny. Yet analysts like Woo argue that Saylor’s long-term conviction and adaptable debt instruments could make the firm a stabilizing force during future bear markets.
As market volatility persists, Strategy’s approach may set a precedent for other public companies seeking Bitcoin exposure without overextending their financial risk.
Editorial Team — CoinBotLab