By Frances Yue
Are investors souring on Michael Saylor's strategy of gobbling up more bitcoin regardless of the price?
Michael Saylor, chairman at Strategy, has led the company's push to raise money and buy bitcoin.
Shares of Strategy, the software company that rose to prominence as a leveraged bet on bitcoin, tallied their lowest close in seven months on Tuesday after bitcoin briefly dipped below $100,000 for the first time since June.
It was the latest disappointing milestone for a stock that a year ago was riding high as President Donald Trump's electoral victory ushered in a wave of enthusiasm for cryptocurrencies. Strategy's decline signals that investors are growing more cautious about Chairman Michael Saylor's playbook for gobbling up more bitcoin, seemingly regardless of the price.
Strategy's stock (MSTR) fell $17.68, or 6.7%, on Tuesday to finish at $246.99, the lowest level since April 8, according to Dow Jones Market Data. Shares have fallen 14.7% year to date, and are down 47.9% from the record closing high of $473.83 reached on Nov. 20, 2024, Dow Jones Market Data showed.
Part of the decline has to do with bitcoin's pullback, as the largest cryptocurrency on Tuesday briefly retreated below $100,000 for the first time since June.
See: Bitcoin slips below $100,000 for first time since June. Here's where it might be headed next.
&#34;Bitcoin's move today does not help the story,&#34; Gus Galá, senior equity research analyst at Monness, Crespi, Hardt &amp; Co., Inc., said in a phone interview with MarketWatch. Bitcoin (BTCUSD) traded at around $100,172 on Tuesday afternoon, roughly 20.3% shy of its record intraday high of $126,272.76 reached on Oct. 6.
But the fact that Strategy - formerly named MicroStrategy - has been under pressure for months suggests that investors may be losing confidence in the company's, well, strategy of frequently raising money to buy more bitcoin, according to Galá. The company has sought to entice investors by issuing debt and stock, capitalizing on the high volatility that comes from holding bitcoin on its balance sheet, which in turn generates active trading opportunities. However, as bitcoin's volatility trends lower overall, that approach has become more challenging, Galá noted in previous interviews.
Premium compresses
The premium of Strategy's shares over the value of the bitcoin it holds has narrowed sharply this year, falling to around 1.25 on Tuesday, down from as high as 8 in 2020, according to data platform StrategyTracker.
The chart below shows how Strategy's multiple to net asset value, which compares a company's market value to the value of the bitcoin it holds, has declined over time.
That premium is a gauge of how much more investors are willing to pay for Strategy's stock compared with the actual value of its bitcoin holdings. A narrowing premium means the market sees less extra value in owning the stock as a way to get bitcoin exposure.
A lowering premium &#34;reduces how accretive MSTR's capital-markets strategy can be,&#34; Brett Knoblauch, analyst at Cantor Fitzgerald &amp; Co., said in a recent report. Put another way, it suggests the company's strategy of employing leverage to buy more bitcoin is becoming less attractive to investors.
There are also concerns that Strategy may continue to dilute existing shareholders, Galá said.
Saylor said during Strategy's third-quarter earnings call on Oct. 31 that the company plans to reduce its overall senior convertible debt outstanding over time and will seek to convert it into equity when that becomes an option.
Bitcoin's decline adds to the pressure
Bitcoin's decline has continued to weigh on Strategy's share price as the broader crypto market struggles to recover from its largest single-day liquidation event of the year, according to Mark Palmer, an analyst at the Benchmark Co. On Oct. 10, at least $20 billion in leveraged positions were wiped out.
Meanwhile, investors have been watching whether the Clarity Act, a bill that aims to establish a comprehensive regulatory framework for crypto, could move forward. But the U.S. government shutdown that began on Oct. 1 has thrown the bill's progress into limbo, Palmer said in comments shared with MarketWatch via email.
Still, Palmer maintains his Buy rating on Strategy. Once liquidity returns to the crypto market and if the U.S. government reopens, it could provide a better setup for bitcoin and for Strategy's stock price as well, he said.
Investors are also watching whether Strategy could be included in the S&amp;P 500 SPX in December, when the index undergoes its quarterly rebalancing, Cantor's Knoblauch said. If that happens, it would likely put upward pressure on Strategy's shares.
Several other crypto-related stocks also fell on Tuesday. Shares of crypto exchange Coinbase (COIN) fell 7% to end at $305.69, FactSet data showed. The stock is now down 27% from its closing high of $419.78 on July 18, although it has fared much better than Strategy in 2025, and remains in positive territory since the start of the year. Shares of bitcoin miner Hut 8 (CA:HUT) sank 12.5% to finish at $48.11, and MARA Holdings (MARA) lost 6.7% to close at $16.62.
U.S. stocks finished lower on Tuesday, with the Dow Jones Industrial Average DJIA falling by more than 250 points, or 0.5%, Dow Jones Market Data showed. The S&amp;P 500 SPX fell 1.2% and the Nasdaq Composite COMP finished 2% lower.
-Frances Yue
This content was created by MarketWatch, which is operated by Dow Jones &amp; Co. MarketWatch is published independently from Dow Jones Newswires and The Wall Street Journal.
(END) Dow Jones Newswires
11-04-25 1824ET

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<p>Shares of Strategy, a software company heavily invested in bitcoin, fell to a seven-month low of $246.99, down 6.7% on Tuesday. This decline follows bitcoin's dip below $100,000, raising concerns about investor confidence in Chairman Michael Saylor's strategy of acquiring more bitcoin regardless of price. The premium of Strategy's shares over the value of its bitcoin holdings has significantly narrowed, indicating reduced investor interest. Analysts suggest that the company's capital-markets strategy may be losing appeal, compounded by broader market volatility and regulatory uncertainties.</p>

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Strategy's stock falls to 7-month low. Why the leveraged bitcoin play is losing steam.