The Saylor Discount: Is MicroStrategy Finally a Value Play?
MicroStrategy (MSTR), a company that has essentially hitched its wagon to Bitcoin, recently saw its stock price dip below its net asset value (NAV). This is a significant event, marking the first time in roughly two years that investors haven't been willing to pay a premium for the company's crypto exposure. A concerning development, particularly given that MicroStrategy's valuation is so tightly coupled with Bitcoin's performance.
The drop below NAV – to be exact, a market-to-NAV ratio of 0.977x – suggests a growing skepticism about MicroStrategy's strategy. Is the market finally calling Saylor's bluff? The core thesis has always been that MicroStrategy is a leveraged play on Bitcoin. But leverage works both ways, and the recent crypto downturn has amplified the downside. The obvious question is: what happens if Bitcoin doesn't rebound to Saylor's projected $150,000 by year-end?
The Billion-Dollar Question: Saylor's Net Worth
Adding another layer to this complex situation is the fact that Michael Saylor, MicroStrategy's executive chairman and biggest evangelist, has seen his personal wealth take a substantial hit. Estimates suggest he's lost over $4 billion in the last six months, largely due to the decline in both Bitcoin's price and MSTR stock.
Forbes estimates Saylor's net worth at $5.9 billion as of November 17, a 41% drop from their $10.1 billion estimate just six months prior. While Forbes doesn't fully disclose their methodology, the estimate likely includes his holdings of MicroStrategy Class B stock and Bitcoin, plus an extra $400 million from other assets.
It's worth remembering that Saylor owns a significant chunk of MicroStrategy's Class B common stock – 19,616,680 shares as of May 2, 2025, which grants him a supervoting power of 43.58%. (This control is a key factor in understanding the company's strategic direction.) He also personally holds a substantial amount of Bitcoin, last disclosed at 17,732 BTC in August 2024.
I've looked at hundreds of these filings, and the lack of updated information on Saylor’s personal Bitcoin holdings is unusual, especially given the current market volatility. Are those holdings unchanged? Did he sell some to cover margin calls elsewhere? We simply don't know.
Doubling Down or Digging Deeper?
Despite the market jitters, Saylor remains bullish. He claims MicroStrategy is accelerating its Bitcoin purchases, framing the selloff as a "temporary dislocation in a long-term secular trend." He even teased another buy announcement.
But here's the crux of the matter: Saylor's confidence doesn't negate the inherent risk. His personal fortune is now inextricably linked to Bitcoin's success. It's a high-stakes game, and the recent NAV dip suggests investors are becoming increasingly aware of the potential downside. As one report notes, MicroStrategy Falls Below Net Asset Value Amid Crypto Crash.
Wall Street analysts seem to be cautiously optimistic, but are they factoring in the full extent of the risk? Are they truly independent in their analysis, or are they swayed by Saylor's charisma and the potential upside? These are questions that need careful consideration.
Saylor’s strategy is akin to a gambler doubling down after a loss. It can lead to enormous gains if the bet pays off, but it also carries the risk of catastrophic losses. MicroStrategy's future, and Saylor's wealth, hangs in the balance.
