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Michael Saylor’s Bitcoin Playbook Backfires on 100+ Companies

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Michael Saylor’s Bitcoin Playbook Backfires on 100+ Companies

Digital asset treasury companies that rushed to copy Michael Saylor’s Bitcoin strategy are now hemorrhaging shareholder value, with median stock prices down 43% year to date, even as the broader market climbs higher, as per .Source: Bloomberg

More than 100 publicly traded companies transformed themselves into cryptocurrency-holding vehicles in the first half of 2025, borrowing billions to buy digital tokens while their stock prices initially soared past the value of the underlying assets they purchased.

The strategy seemed unstoppable until market reality delivered a harsh correction.Strategy’s Model Spawns Industry-Wide Collapse

Strategy Inc.’s Michael Saylor pioneered the approach of converting corporate cash into Bitcoin holdings, transforming his software company into a publicly traded cryptocurrency treasury.

The model worked spectacularly through the mid-2025, attracting high-profile investors, including the Trump family.

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SharpLink Gaming epitomized the frenzy. The company pivoted from traditional gaming operations, appointed an Ethereum co-founder as chairman, and announced massive token purchases.

💰Sharplink Gaming added $80M in Ether to its reserves, lifting total holdings to $3.6B and cementing its spot as the second-largest corporate holder of ETH. — Cryptonews.com (@cryptonews)

Its stock exploded 2,600% within days before crashing 86% from peak levels, leaving total market capitalization below the value of its Ethereum holdings at just 0.9 times crypto reserves.

Bloomberg data tracking 138 U.S. and Canadian digital asset treasuries shows the median share price has fallen 43% year-to-date, dramatically underperforming Bitcoin’s modest 7% decline.

In comparison, the S&P 500 gained 6% and the Nasdaq 100 rose 10%.

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Strategy shares have dropped 60% from their July highs, even as they have risen by more than 1,200% since the company began buying Bitcoin in August 2020.Source: Bloomberg

“Investors took a look and understood that there’s not much yield from these holdings rather than just sitting on this pile of money,” B. Riley Securities analyst Fedor Shabalin told Bloomberg.Debt Obligations Expose Structural Flaws

The fundamental problem plaguing these companies stems from how they fund cryptocurrency purchases.

Strategy and its imitators issued massive amounts of convertible bonds and preferred shares, raising over $45 billion across the industry to acquire digital tokens that generate no cash flow.

These debt instruments carry substantial interest and dividend obligations that cryptocurrency holdings cannot service, creating a structural mismatch between liabilities that require regular payments and assets that produce zero income.

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Strategy faces annual fixed obligations of approximately $750 million to $800 million tied to preferred shares.

Companies that avoided Bitcoin for smaller, more volatile cryptocurrencies suffered the steepest losses.

Alt5 Sigma, backed by two Trump sons and planning to purchase over $1 billion in World Liberty Financial’s WLFI token, has crashed more than 85% from its June peak.Source:

Strategy attempted to address funding concerns by raising $1.44 billion in dollar reserves through stock sales, covering 21 months of dividend payments.Saylor Admits Potential Bitcoin Sales

The industry now faces its defining moment. Strategy CEO Phong Le the company would sell Bitcoin if needed to fund dividend payments, specifically if the firm’s market value falls below its cryptocurrency holdings.

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Those comments sent shockwaves through the digital asset treasury sector, given Saylor’s repeated insistence that Strategy would never sell, famously joking in February to “sell a kidney if you must, but keep the Bitcoin.“

At December’s Binance Blockchain Week, Saylor the revised approach, stating that “when our equity is trading above the net asset value of the Bitcoin, we just sell the equity,” but “when the equity’s trading below the value of the Bitcoin, we would either sell Bitcoin derivatives, or we would just sell the Bitcoin.“

The reversal raises fears of a downward spiral where forced crypto sales push token prices lower, further pressuring treasury company valuations and potentially triggering additional selling.

Strategy’s monthly Bitcoin accumulation has collapsed from 134,000 BTC at the 2024 peak to just 9,100 BTC in November, with only 135 BTC added so far in December.

The company now holds approximately 650,000 BTC, valued at over $56 billion, representing more than 3% of Bitcoin’s maximum supply.

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Market participants worry that leveraged traders using borrowed money to invest in these companies could face margin calls, forcing broader market selloffs.

Strategy has created a $1.4 billion reserve fund to cover near-term dividend payments, but shares remain on track for a 38% decline this year despite the company’s massive Bitcoin holdings.

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Crypto

Disappointed By Bitcoin And Dogecoin In 2025? These Coins Soared Over 2000% To Dominate The Gainers List

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Disappointed By Bitcoin And Dogecoin In 2025? These Coins Soared Over 2000% To Dominate The Gainers List

Amid a year of big losses for major large-cap cryptocurrencies, two under-the-radar tokens captured the market’s attention by delivering eye-popping returns.

The Unprecedented Surge

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Solana (CRYPTO: SOL)-based memecoin pippin (PIPPIN) skyrocketed 5384% in 2025 to become the cryptocurrency market’s biggest gainer of the year.

Largely dormant throughout the year, the coin ignited an explosive rally around mid-November, culminating in an all-time high of $0.6109 last week.

PIPPIN was launched as a viral AI-generated unicorn image by Yohei Nakajima, creator of the autonomous AI agent BabyAGI. After going viral on social media, the community decided to transition the token into an autonomous AI agent on X.

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Cryptocurrency YTD Gains +/- Price (Recorded at 8:14 p.m. ET)
pippin +5384.24% $0.4212
AB +2716.16% $0.004567

See Also: Bitcoin Failed As ‘Store Of Value’ In 2025, But These Crypto Derivatives Of Gold, Silver Delivered Sharp Returns — Check Them Out

Similarly, AB (AB) token rallied 2716%, emerging as the second-most successful cryptocurrency of the year. Unlike PIPPIN, the coin erupted to new highs in early 2025 but lost its footing in the later stages.

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AB, formerly known as Newton Project, is a modular blockchain ecosystem focused on cross-chain interoperability and real-world asset integration. The native token is used for paying transaction fees, executing smart contracts and enabling governance.

These towering gains stood in stark contrast to the losses endured by more popular assets like Bitcoin (CRYPTO: BTC) and Dogecoin (CRYPTO: DOGE), which lost their way in the last quarter of the year following robust rallies earlier.

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While Bitcoin lost 4.59% year-to-date, Dogecoin has bled 60% since 2025 started.

Read Next: 

Photo Courtesy: Alexandru Nika on Shutterstock.com

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Market News and Data brought to you by Benzinga APIs

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Landmark Crypto Bills Drive 2025 Regulatory Shift as Congress Signals Commitment to Digital Asset Growth

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Landmark Crypto Bills Drive 2025 Regulatory Shift as Congress Signals Commitment to Digital Asset Growth
U.S. crypto regulation advanced sharply in 2025 as Congress set stablecoin rules, embraced regulated digital finance and accelerated market structure efforts, marking a broad legislative push that brought long-sought clarity to digital assets.
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Bitcoin price retraces 30% from record high. How does crypto market look like in 2026? | Stock Market News

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Bitcoin price retraces 30% from record high. How does crypto market look like in 2026? | Stock Market News

The year 2025 has remained mixed for the crypto market as the sector presents a balanced yet optimistic outlook. Looking at the positive side, there was tangible advancement—DeFi ecosystems continued to grow, stablecoins gained wider traction, CBDC infrastructure pilots moved forward, and developer participation surged across APAC and worldwide, with millions building on-chain.

“On one hand, the industry saw real progress: growth in DeFi projects, expansion of stablecoins, new CBDC-infrastructure pilots, and rising developer activity across APAC and globally, with millions committing to code on-chain. On the other hand, after early-year optimism from retail investors, the October correction was a reminder that sentiment remains fragile and that hype without real delivery can still hurt the industry,” said Nischal Shetty, Founder, WazirX.

Bitcoin has fallen roughly 30% from record high levels and is down more than 6% so far this year, as the market continues to find it difficult to recover after the October crash. According to Bloomberg report, trading activity remains subdued, with retail speculation losing momentum.

The decline has partly been driven by technical factors, with prices dropping below the 365-day moving average, while persistent selling by long-term holders has also weighed on Bitcoin.

Key drivers of the crypto market in 2025

At the beginning of the year, the market witnessed the setup of US Strategic Bitcoin Reserve, underscoring Bitcoin’s rising strategic significance.

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By mid-year, the enactment of the GENIUS Act introduced a well-defined regulatory framework for USD-backed stablecoins, strengthening confidence and paving the way for wider adoption.

The CFTC’s December 4 decision to permit listed spot crypto products on registered futures exchanges represented a key milestone, advancing the market from regulated ETFs toward more transparent cross-border compliance structures and greater institutional involvement.

Crypto market outlook in 2026

According to Shetty, global institutional appetite for regulated digital-asset products will continue to increase, driving capital inflows and contributing to market stability.

At the same time, domestic policies for countries will be key in shaping their respective investor sentiment. In India, the foundation stone of the CBDC project could be laid soon, Shetty added.

“The RBI has announced a hackathon in October to nurture tech talents in the emerging technology space, which will encourage more Indians to see emerging tech as a promising career prospect. A clearer regulatory framework for VDAs, potentially paired with supportive tax measures, support for stablecoin initiatives alongside CBDC measures, could unlock real-world blockchain use cases from Indian builders to kickstart on-chain growth for Indians,” Shetty said.

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Disclaimer: This story is for educational purposes only. The views and recommendations above are those of individual analysts or broking companies, not Mint. We advise investors to check with certified experts before making any investment decisions.

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