Willy Woo's Strategy to Survive the Next Bitcoin Bear Market

Willy Woo: Strategy Remains Firm During Next Bitcoin Bear Market

5 November 2025 at 09: 06

Reading time: 2 minutes

Michael Saylor's strategy with MicroStrategy (MSTR) appears significantly liquidation-resistant, even in the event of a future cryptocurrency downturn. Bitcoin analyst Willy Woo stated on social media that he doubts MSTR will be forced to sell any of its Bitcoin reserves in a future bear market.

MicroStrategy currently has approximately $1,01 billion of debt maturing on September 15, 2027. To prevent the company from Bitcoin (BTC) needs to sell to pay off the debt, the market price of its shares needs to be above $183,19, according to Woo. This would imply a Bitcoin price around $91.502, with an assumed net asset value (mNAV) multiple of 1.

Analyst The Bitcoin Therapist emphasizes that it's unlikely MicroStrategy will need to sell Bitcoin, even in a substantial market correction. "Bitcoin would have to perform poorly to force MSTR to liquidate," he noted. Currently, MicroStrategy holds approximately 641.205 Bitcoin, worth an estimated $64 billion, according to the Saylor Tracker. Contrary to these positive sentiments, MSTR's share price hit a seven-month low on Tuesday, dropping 6,7% to $246,99. Bitcoin itself has fallen 9,92% over the past week and is currently trading around $101.377.

The possibility of partial liquidation

While Willy Woo doesn't expect a liquidation in the projected bear market, he points to the possibility of one if Bitcoin doesn't rise fast enough in the expected 2028 bull market. "Ironically, there's a chance of partial liquidation if BTC doesn't rise fast enough in an assumed 2028 bull market," Woo said.

Several prominent figures in the crypto space, such as Cathie Wood, CEO of ARK Invest, and Brian Armstrong, CEO of Coinbase, predict that Bitcoin could potentially reach $1 million by 2030. Such predictions highlight the speculative nature of the market and the unpredictability of price movements. It remains crucial for investors to closely monitor developments surrounding MicroStrategy and the broader crypto market.

Frequently Asked Questions

What are the implications of MicroStrategy's debt structure for investors?
Investors should be aware that MicroStrategy's debt can be converted into cash and stock, which can minimize the need to sell Bitcoin. This offers a degree of protection against liquidation in a bearish scenario.

How could a bearish market impact MicroStrategy?
Should the Bitcoin price fall significantly, the value of MicroStrategy's Bitcoin reserves would also decline, which could strain the company's ability to service its debt. However, as long as the share price remains above the critical level, liquidation seems unlikely.

What are the expectations for Bitcoin until 2030?
With projections like those from Cathie Wood and Brian Armstrong, who estimate Bitcoin to be worth a million dollars, investors should prepare for a volatile but potentially lucrative future in the crypto space, where price movements and market dynamics will continue to challenge them.

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