The playbook for corporate Bitcoin accumulation has largely followed one template: issue convertible debt, buy Bitcoin, repeat. Strive CIO Ben Werkman thinks that template has a fatal flaw.

During a podcast on November 18, 2025, Werkman laid out his case against the convertible debt structures that have become the go-to financing tool for Bitcoin treasury companies. His core argument: if crypto prices stay depressed or even just flat for an extended period, the maturity and repayment pressures embedded in those instruments could create serious problems for the companies that issued them.

The convertible debt problem, explained

Here’s how convertible bonds typically work in this context. A company issues debt that investors can later convert into equity, usually at a premium to the current stock price. The company gets cheap capital (often at below-market interest rates) because investors are betting the stock will rise enough to make conversion attractive. If the stock doesn’t rise, the company has to repay the debt in cash.

Werkman pointed to a significant increase in convertible bond issuance among Bitcoin treasury companies. The volatility in underlying equities, particularly those like Strategy (the company formerly known as MicroStrategy), makes these instruments especially risky. When Bitcoin drops, these companies’ stock prices tend to drop harder. And when stock prices fall below conversion thresholds, what was once cheap financing becomes expensive debt that needs to be serviced or repaid.

Strive’s alternative approach

Werkman isn’t just critiquing from the sidelines. Strive has deliberately avoided convertible debt entirely, opting instead for PIPE (Private Investment in Public Equity) financing and preferred stock offerings, including instruments called SATA shares, to fund its Bitcoin accumulation strategy.

The difference matters. PIPE financing and preferred stock don’t carry the same ticking-clock repayment obligations that convertible bonds do. There’s no maturity date where you suddenly need to come up with hundreds of millions in cash. The trade-off is that these instruments can be more dilutive to existing shareholders, but Werkman’s view appears to be that dilution beats insolvency.

Strive has been putting its money where its mouth is. In January 2026, the company retired approximately $110 million of Semler Scientific debt, including $90 million of 4.25% convertible senior notes due in 2030. That same month, Strive purchased 333.89 BTC at an average cost of roughly $89,851 per coin.

The company’s total Bitcoin holdings now stand at 13,131.82 BTC, placing it among the top 10 publicly traded corporate holders of the asset.

Why Werkman’s background matters here

Werkman was appointed CIO at Strive on October 6, 2025, bringing a background in distressed credit and treasury strategy from previous roles at Swan Bitcoin and NumerisX.

Strive’s broader leadership team reinforces this cautious-but-committed approach. The company’s board includes multiple Bitcoin treasury executives, such as Pierre Rochard of The Bitcoin Bond Company.

What this means for investors

The convertible debt question is becoming one of the most important risk factors in evaluating Bitcoin treasury companies. For investors evaluating Bitcoin treasury stocks, the capital structure deserves as much scrutiny as the Bitcoin holdings themselves. A company holding 50,000 BTC with $2 billion in convertible notes maturing next year is in a fundamentally different risk position than a company holding 10,000 BTC with no debt maturities on the horizon.

Strive’s approach of using PIPE financing and preferred stock offerings represents one alternative model. It demonstrates that companies can accumulate significant Bitcoin positions — 13,131.82 BTC — without taking on the maturity risk that convertible bonds carry.