Navigating the Bitcoin Rollercoaster: Is Strategy (MSTR) a Buy, Sell, or Hold?

Bitcoin’s Rollercoaster: Strategy’s Bumpy Ride Amid Market Turmoil

June 24, 2023 — If you thought owning Bitcoin was a wild ride, just ask Strategy (formerly MicroStrategy). The enterprise software company, now a major player in the Bitcoin treasury game, has seen its fortunes fluctuate dramatically over the past eight months. Since reaching a staggering peak of $126,198.07 in October 2022, Bitcoin has plummeted by 52%, leaving investors grappling with uncertainty.

As the world’s largest holder of Bitcoin, with a staggering 847,363 units on its balance sheet, Strategy has felt the brunt of this downturn. Once a darling of the stock market, its share price has soared by 723% over the past six years, but it now languishes 80% below its all-time high, trading below $100 for the first time since early 2024.

Weak Sentiment for Digital Credit

One of Strategy’s key strategies for accumulating Bitcoin has been through its STRC perpetual preferred equity offering, which billionaire founder Michael Saylor refers to as “digital credit.” Launched in July 2025, this ambitious initiative has raised an impressive $10.5 billion, marking it as one of the largest preferred equity offerings in history.

Designed for investors seeking steady income, STRC aims to mitigate the volatility and principal loss risks associated with Bitcoin. Currently, shareholders receive $11.52 in annual dividends, translating to an effective yield of 15.4%. However, the sentiment surrounding STRC has soured, with its price dropping to $74.57 from a par value of $100 since late May. This decline raises concerns about Strategy’s financial stability and its ability to raise further capital through STRC.

Despite these challenges, Strategy has maintained its commitment to dividend payments, with the next payout scheduled for July 15. Meeting this obligation could signal to the market that the company’s financial engine is still running smoothly.

Today’s Market Snapshot

• Current Price: $82.50 (-3.31%, down $2.83)
• Market Cap: $30 billion
• Day’s Range: $81.82 – $87.61
• 52-Week Range: $81.82 – $457.22
• Volume: 2.1 million
• Average Volume: 19.4 million
• Gross Margin: 68.11%

High Risk, High Reward

Investors should brace themselves for volatility. Strategy is effectively a leveraged bet on Bitcoin, amplifying both potential gains and losses. With shares trading around $94, some might see this as an enticing opportunity, especially given the company’s diluted market cap of $29.4 billion, which is near an all-time low compared to the $51.6 billion worth of Bitcoin it holds.

Moreover, Strategy boasts a cash reserve of $1.4 billion, providing a safety net to meet its obligations if needed. For long-term investors willing to weather the storm, now may be the time to consider buying shares—albeit with caution and appropriate position sizing.

As the cryptocurrency landscape continues to evolve, Strategy’s journey serves as a stark reminder of the inherent risks and rewards in the world of digital assets. Will the market sentiment shift in favor of Bitcoin and its largest holder? Only time will tell.