The growing trend of companies stockpiling Bitcoin and other tokens on their balance sheets is now being compared to the risky financial engineering that preceded the 2008 crash.
Milo CEO and former Goldman Sachs analyst Josip Rupena cautions that corporate treasuries holding digital assets may unintentionally introduce layers of risk that investors aren’t fully aware of.
Bitcoin itself is a clean, counterparty-free asset, but when folded into a corporate structure, Rupena says it inherits new vulnerabilities — management competence, debt obligations, cybersecurity, and the sustainability of revenue streams. In short, investors may think they’re backing Bitcoin, but in reality, they’re exposed to a company’s entire risk profile.
While Rupena doesn’t expect treasuries to cause the next market collapse, he warns that firms carrying heavy leverage could magnify losses if forced to liquidate holdings during a downturn. With 178 publicly traded companies now holding Bitcoin, a rush to sell could ripple across the market in ways that resemble past contagion events in traditional finance.
This possibility has analysts questioning whether treasuries might act as accelerants rather than stabilizers. If Bitcoin dips sharply, a wave of forced sales could overwhelm liquidity and drive prices lower than natural market forces would otherwise dictate.
The playbook that began with Michael Saylor’s MicroStrategy has now spread far beyond Bitcoin. In recent months, firms have started diversifying treasuries into altcoins such as Solana, XRP, Dogecoin, and Toncoin.
The results so far highlight the volatility of this strategy. Some companies enjoyed short-lived hype, while others were punished by markets. Safety Shot, a beverage maker, saw its stock crater by 50% after announcing it would hold BONK as its main reserve asset. Even established Bitcoin treasury firms have seen their shares slump in recent months, showing that investors remain skeptical of the long-term stability of such strategies.
Speculation is mounting that crypto treasuries may be creating a parallel bubble — one that’s not purely tied to Bitcoin’s fundamentals but to corporate adoption trends. As more companies rush to announce treasuries, competition for attention may be inflating valuations without delivering real utility.
If Bitcoin continues to trend upward, these companies could multiply their returns and attract even more followers. But if the market falters, widespread sell-offs could hit both crypto prices and equity valuations, potentially creating a double-edged crisis.
For now, investors appear torn between excitement at the mainstreaming of crypto treasuries and anxiety that history may be repeating itself — with complex structures hiding risks until it’s too late.
