Grayscale Calls on Strategy to Sell Part of Bitcoin Stack
Strategy Inc.'s Bitcoin treasury strategy is facing renewed scrutiny after Grayscale's head of research suggested the company should consider selling a portion of its holdings to strengthen its balance sheet instead of relying on increasingly expensive financing.
Summary
- Grayscale’s Zach Pandl said Strategy should consider selling more than $3 billion in Bitcoin to improve liquidity.
- Investors remain focused on the company’s preferred stock and roughly $1.2 billion in annual dividend obligations.
- Strategy continues accumulating Bitcoin, with total holdings reaching 847,363 BTC despite mounting market scrutiny.
The comments come as Strategy’s preferred securities continue trading below par and investors debate whether the company’s debt-funded Bitcoin acquisition model remains sustainable during an extended market downturn. Executive Chairman Michael Saylor, however, has shown no indication of abandoning the firm’s long-standing accumulation strategy.
Grayscale Calls for Balance Sheet Reset
The latest debate surrounding Strategy’s capital structure was sparked by comments from Grayscale Head of Research Zach Pandl, who argued the company should consider selling more than $3 billion worth of Bitcoin to strengthen its financial position.
For Strategy $MSTR next week
*what I think happens: increase in $STRC dividend of 50bp, which equates to ~$100mn higher dividend obligation for next 2yrs; probably does not help market confidence
*what I hope happens: sale of ≥ ~$3bn $BTC to cover nearly all cash obligations… https://t.co/8KyZpIBxFL
— Zach Pandl (@LowBeta) June 27, 2026
Pandl suggested that using a portion of Strategy’s digital asset holdings to meet cash obligations could help restore investor confidence more effectively than relying on additional preferred-share financing. His proposal represents one of the clearest institutional arguments yet for Strategy to prioritize liquidity management over continued Bitcoin accumulation.
The recommendation stands in contrast to Strategy’s long-standing philosophy under Executive Chairman Michael Saylor, who has consistently promoted Bitcoin as a long-term treasury reserve asset rather than one to be sold during periods of market weakness.
Although Strategy sold 32 BTC earlier this month to help fund preferred dividend payments, management characterized the transaction as an isolated event rather than a strategic shift away from its buy-and-hold approach.
Financing Model Faces Growing Pressure
The discussion comes as investors continue evaluating the sustainability of Strategy’s financing model, which has relied on issuing common shares and preferred securities to fund additional Bitcoin purchases.
The company currently faces approximately $1.2 billion in annual preferred dividend obligations, while its STRC preferred shares have traded at a significant discount to their $100 par value in recent weeks. The decline has fueled broader questions over investor demand for the company’s financing instruments amid higher interest rates and weaker cryptocurrency prices.
READ MORE: Fidelity Challenges Fears Over Bitcoin’s Long-Term Security
Several market observers have argued that Strategy should preserve liquidity rather than continue expanding its Bitcoin position. CryptoQuant analysts have also suggested the company pause additional purchases to rebuild its cash reserves after a decline in available dollar liquidity during the first half of the year.
The increased attention follows weeks of heightened volatility across both Bitcoin and Strategy’s securities, as investors reassess the risks associated with highly leveraged corporate Bitcoin treasury strategies.
Bitcoin Treasury Continues to Expand
Despite the criticism, Strategy has shown no indication that it plans to slow its accumulation strategy.
According to data shared by Saylor over the weekend, the company now holds 847,363 BTC, with a market value of approximately $50.88 billion. Strategy’s average purchase price stands at $75,653 per Bitcoin, leaving the overall position roughly 20.6% below cost at current market prices.
The visualization, published alongside Saylor’s social media post stating, “We’re gonna need more charts, illustrates more than 113 separate Bitcoin purchase events completed since the company adopted its treasury strategy in 2020.
We’re gonna need more charts. pic.twitter.com/xVASOEnSw8
— Michael Saylor (@saylor) June 28, 2026
With Bitcoin currently trading near $60,000, most acquisitions completed throughout 2024, 2025 and 2026 remain unrealized losses. Even so, Strategy continued adding to its position this month, including a purchase of 520 BTC, reinforcing management’s commitment to its long-term Bitcoin strategy despite mounting pressure from some institutional observers.
Institutional Debate Over Corporate Bitcoin Treasuries
The differing views between Strategy and Grayscale reflect a broader debate over how corporate Bitcoin treasury companies should balance long-term conviction with capital management.
Supporters of Strategy argue that maintaining exposure through market cycles has historically rewarded long-term shareholders and reinforces Bitcoin’s role as a strategic reserve asset. Critics, however, contend that companies using leverage and preferred securities to finance purchases face greater pressure to preserve liquidity when market conditions deteriorate.
As more publicly traded firms adopt Bitcoin treasury strategies, investors are increasingly evaluating not only the size of digital asset holdings but also the sustainability of the financing structures supporting them.
For now, Saylor continues signaling confidence in Strategy’s approach, while Grayscale’s proposal highlights the growing institutional discussion over whether preserving balance-sheet flexibility should take precedence over continued Bitcoin accumulation during periods of prolonged market weakness.
The information presented in this article is intended for informational purposes only and should not be interpreted as financial, investment, or trading advice. Coinspress.com does not promote or advocate for any particular investment strategy, asset, or cryptocurrency project. Cryptocurrency markets are highly volatile and unpredictable – always perform your own research and seek guidance from a qualified financial professional before making any investment decisions.
Alexander Zdravkov
Reporter at CoinsPress
Alexander Zdravkov is a market analyst and crypto journalist with interests in economics, broader financial markets and digital assets. His journey into crypto began more than four years ago, driven by a fascination with the rapid evolution of blockchain technology and the transformative potential of decentralized finance. He began analyzing market cycles and identifying emerging trends before they reach the mainstream. He holds a degree in International Relations - a background that helped shape his broader perspective on global economics, geopolitics, and the interconnected nature of modern financial markets. Whether covering the latest developments in the crypto sector or exploring broader macroeconomic themes, Alexander focuses on giving readers context rather than simply repeating headlines. During his career, he has authored more than 10,000 articles covering cryptocurrencies, traditional finance, and global market developments. His work spans everything from Bitcoin and altcoins to macroeconomic trends influencing risk assets worldwide.
