Smaller public companies holding Bitcoin have failed to replicate MicroStrategy's success. Their model depends on Bitcoin's price rising consistently to allow for more debt issuance and acquisitions. The recent sideways market has broken this flywheel, collapsing their valuations into 'Bitcoin penny stocks.'

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As Bitcoin matures, its risk-return profile is changing. The era of doubling in value every couple of years may be over. Instead, it could transition into a high-performing asset that reliably generates 15-25% annualized returns, outperforming traditional assets but no longer offering the explosive, "get rich quick" upside of its early days.

When a company's valuation is based on profits projected decades into the future, it reaches a critical point. Investors eventually stop buying into even more distant projections, causing a stall as they wait for reality to catch up or sell to others who still believe.

Drawing parallels to closed-end funds, Berkshire Hathaway, and well-managed banks, analyst Andy Edstrom argues against high MNAV (multiple of net asset value) multiples for Bitcoin treasury companies. Historical precedent suggests these firms should trade between a slight discount (0.8x) and a modest premium (2-2.5x MNAV), not the extreme valuations seen previously.

Analyst Andy Edstrom categorizes most Bitcoin treasury companies, excluding MicroStrategy, as "dumpster fires." He attributes their failure to inexperienced CEOs, reporting issues, a lack of cash flow to service debt, and consequently, catastrophic stock price collapses of 80-95% from their peaks.

A proposed mental model frames MicroStrategy's issuance of preferred stock as analogous to Tether issuing stablecoins. Instead of using treasuries, MSTR uses heavily over-collateralized Bitcoin (e.g., 5-to-1 ratio) to create a yield-bearing, dollar-denominated instrument, effectively securitizing its Bitcoin holdings to generate returns for equity holders.

As a highly volatile and retail-driven asset, Bitcoin serves as a leading indicator for investor risk appetite. It's a "canary in the coal mine" where a "risk on" sentiment leads to sharp increases, while a "risk off" mood triggers rapid declines, often preceding moves in traditional markets.

Instead of simply holding Bitcoin, MicroStrategy layered on complex debt instruments like preferred stock. This convolution made it difficult for investors to understand the true risk and preference stack, contributing to the stock trading at a discount to its own assets when sentiment turned. Simplicity is safer.

Bitcoin's 27% plunge, far exceeding the stock market's dip, shows how high-beta assets react disproportionately to macro uncertainty. When the central bank signals a slowdown due to a "foggy" outlook, investors flee to safety, punishing the riskiest assets the most.

The recent divergence, where Bitcoin has fallen significantly while major stock indices remain stable, breaks the asset's recent high correlation with risk-on equities. This suggests the current bearish sentiment is isolated to the crypto asset itself and its specific market dynamics, rather than being part of a broader market-wide downturn.

An investor's Bitcoin thesis rests on three pillars: 1) as a self-custodied asset for debanking/borderless scenarios, 2) as an investment for pure price appreciation ("number go up"), and 3) as an ethical holding to support a better financial system. This framework clarifies why proxies like MSTR satisfy the latter two needs but never the first.

Bitcoin Treasury Companies Falter Where MicroStrategy Succeeded Due to Sideways Price Action | RiffOn