How MicroStrategy Lost Reddit’s Retail Investors in Weeks

By Trey Thoelcke Published Jul 17, 8:10AM EDT

Quick Read

MSTR shares crashed 79% over the past year while Reddit sentiment collapsed from 94 (very bullish) to deeply bearish in just weeks.
Strategy sold bitcoin to cover annual preferred dividend obligations totaling somewhere between $750 million and $800 million, a drag that BlackRock and Fidelity spot bitcoin ETFs do not carry.
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How MicroStrategy Lost Reddit’s Retail Investors in Weeks — © 24/7 Wall St.

Retail enthusiasm for Strategy (NASDAQ:MSTR | MSTR Price Prediction), still commonly known as MicroStrategy, has curdled in weeks. Shares closed at $94.03 on Thursday, down about 3.5% on the day, off over 23% in the past month, and down more than 79% over the past year. Reddit sentiment mirrors the slide: the Reddit sentiment score collapsed from 94 (very bullish) on June 30 to a range of 18 to 28 (bearish to very bearish) this week.

On July 5, Strategy disclosed the sale of 3,588 bitcoin worth roughly $225 million to fund preferred stock dividends, a move retail investors read as the first material crack in the leveraged bitcoin treasury model. Bitcoin itself is near $62,900, down 47% year over year, and MicroStrategy’s Q1 2026 EPS of −$38.25, missing expectations, driven by a $14.46 billion unrealized loss on digital assets.

Reddit’s Mood Snapped on the Bitcoin Sale

Discussion volume peaked on June 30 with 4,247 upvotes and 322 comments, then flipped bearish as the liquidation post from user Kazgarth_ pulled in 2,923 upvotes and 340 comments on r/wallstreetbets. r/investing piled on with a fundamentals critique, arguing that Strategy now “trades below the value of its btc holdings and the premium that made the model work has flipped to a discount.”

Michael Saylor’s ‘Strategy’ sold another 3,588 Bitcoin worth $225 million.
by u/Kazgarth_ in wallstreetbets

The bear case retail investors are coalescing around:

Strategy is selling bitcoin to cover $750 million to $800 million in annual preferred dividend obligations, with $229.53 million paid in Q1 2026 alone.
The firm carries $8.17 billion in long-term debt and raised $11.68 billion year to date in fresh equity, diluting common holders.
Bitcoin’s average cost basis of $75,699 now stands well above spot, turning debt refinancing expensive.

The tone has shifted from euphoria to gallows humor. One July 16 post titled “Volatility is Vitality” chronicled a friend whose $540,000 position, valued at its November 2024 peak, evaporated after rolling calls forward.

MicroStrategy vs. the Spot ETF Alternative

Polymarket traders are pricing the near term tightly: the $105 upside strike carries just 21% odds this week. Spot bitcoin ETFs from BlackRock and Fidelity offer direct exposure without the preferred dividend drag, an alternative that did not exist during Strategy’s 2024 bull run. With BTC weakness persisting, watch the next preferred stock issuance and any further bitcoin sales as the tell on whether management’s “intelligent leverage” thesis still holds.

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About the Author Trey Thoelcke →

Trey has been an editor and author at 24/7 Wall St. for more than a decade, where he has published thousands of articles analyzing corporate earnings, dividend stocks, short interest, insider buying, private equity, and market trends. His comprehensive coverage spans the full spectrum of financial markets, from blue-chip stalwarts to emerging growth companies.

Beyond 24/7 Wall St., Trey has created and edited financial content for Benzinga and AOL's BloggingStocks, contributing additional hundreds of articles to the investment community. He previously oversaw the 24/7 Climate Insights site, managing editorial operations and content strategy, and currently oversees and creates content for My Investing News.

Trey's editorial expertise extends across multiple publishing environments. He served as production editor at Dearborn Financial Publishing and development editor at Kaplan, where he helped shape financial education materials. Earlier in his career, he worked as a writer-producer at SVE. His freelance editing portfolio includes work for prestigious clients such as Sage Publications, Rand McNally, the Institute for Supply Management, the American Library Association, Eggplant Literary Productions, and Spiegel.

Outside of financial journalism, Trey writes fiction and has been an active member of the writing community for years, overseeing a long-running critique group and moderating workshop sessions at regional conventions. He lives with his family in an old house in the Midwest.