Brad Garlinghouse slams Michael Saylor’s Bitcoin funding strategy

Brad Garlinghouse has criticized Michael Saylor’s Bitcoin acquisition strategy, arguing that Strategy’s reliance on preferred stock financing has failed to create lasting value as its securities continue to weaken.

According to comments made during a CNBC interview on Friday, Ripple CEO Brad Garlinghouse criticized Michael Saylor’s approach to financing Bitcoin purchases through Strategy’s capital markets program, saying long-term value in crypto should come from real-world utility rather than financial engineering.

Questioning whether the model can continue rewarding shareholders over time, Garlinghouse argued that issuing securities to fund additional Bitcoin purchases does not create sustainable value. He added that Strategy’s focus on financial structuring has had negative consequences for the digital asset market.

Although he challenged Strategy’s funding model, Garlinghouse maintained that he remains bullish on Bitcoin itself. His comments came as Bitcoin briefly traded below $60,000 on Friday, extending pressure across companies closely tied to the cryptocurrency.

Strategy’s preferred stock has come under pressure

Garlinghouse pointed to Strategy’s STRC preferred shares as evidence that investors are becoming more cautious about the company’s financing structure. He noted that the preferred stock has fallen roughly 25% below its $100 face value, describing the decline as a sign that investors are questioning the sustainability of the approach.

Strategy has spent roughly the past year raising capital through preferred securities, including STRC, to finance additional Bitcoin purchases. The instrument also carries an 11.5% cumulative annual dividend obligation, leaving the company with continuing dividend commitments alongside its expanding Bitcoin treasury.

At the same time, scrutiny has widened beyond Garlinghouse’s criticism. Earlier this week, on-chain analytics firm CryptoQuant recommended that Strategy pause further Bitcoin purchases and instead strengthen its cash reserves as market conditions remain difficult.

Additional pressure has emerged from legal developments. As crypto.news reported previously, Rosen Law Firm has opened an investigation into whether Strategy made materially inaccurate business disclosures to investors. According to the firm, it is evaluating potential securities claims and considering a possible class action lawsuit on behalf of shareholders who suffered losses.

Investor scrutiny has continued despite mixed market signals

Selling by company insiders has added another layer to investor concerns. SEC filings show Strategy director Jarrod Patten exercised options to acquire 1,500 Class A shares on June 23 before selling the entire position the same day at $106.08 per share, generating an estimated pre-tax gain of about $131,766.

The latest transaction extends a months-long selling streak. Regulatory filings indicate Patten has sold 55,750 Strategy shares over the past three months for roughly $9 million in proceeds, with the sales taking place as investors continue debating the company’s reliance on repeated share issuance and leveraged Bitcoin accumulation.

Even so, derivatives markets are not signaling expectations of an immediate company-specific crisis. According to new research from Anchorage Digital, traders continue paying elevated premiums for downside protection across Bitcoin, BlackRock’s iShares Bitcoin Trust and Strategy shares, but options pricing remains well below levels seen during previous periods of severe stress.

Anchorage Digital’s head of research, David Lawant, wrote that while defensive positioning has risen into the upper range of historical readings, Strategy’s options market has not reached the conditions normally associated with forced deleveraging or fears of a breakdown in the company’s business model.