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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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XRP Holds Technical Footing as Ripple’s Expanding Global Regulatory Footprint Strengthens Bullish Narrative

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XRP Holds Technical Footing as Ripple’s Expanding Global Regulatory Footprint Strengthens Bullish Narrative
XRP holds a pivotal support zone as price steadies after a pullback, with tightening volatility, neutral momentum signals, and Ripple’s expanding European regulatory approvals reinforcing confidence that consolidation may be setting the stage for the next directional move.
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Inside the botched launch of ex-NYC Mayor Eric Adams’ new crypto token

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Inside the botched launch of ex-NYC Mayor Eric Adams’ new crypto token

For a moment, Eric Adams was riding high.

Fresh off trips to Dubai and the Democratic Republic of Congo, the now jobless ex-mayor of New York City was back in Times Square on Monday to announce his first initiative as a private citizen: a new cryptocurrency coin that would also serve to beat back antisemitism and “anti-Americanism.”

“We’re about to change the game,” he promised, without describing how, exactly, the digital asset would support those lofty ambitions. “This thing is going to take off like crazy.”

But after surging to a nearly $600 million valuation within minutes of its launch, the new coin, dubbed NYC Token, went into free fall, losing nearly 75% of its value by that evening. The drop came after an account linked to the token’s creation withdrew $2.5 million worth of coins, according to the crypto-analytics firm Bubblemaps.

Around $1.5 million was later returned, the firm said, though by then investor confidence had collapsed. To some cryptocurrency experts, the rollout had all the hallmarks of a “rug pull.” The scheme — prevalent among celebrity-linked meme coins — involves insiders hyping an asset then quickly dumping their stakes, saddling amateur investors with deep losses.

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Others have suggested that Adams and his inexperienced team were themselves duped by savvier investors, who took advantage of a sloppy launch.


News 4

News 4

Former Mayor Eric Adams launches “NYC Token” from Times Square, a cryptocurrency he claims will fund efforts to fight antisemitism.

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The debate has found Adams back in a mode of damage control that defined so much of his one-term mayoralty: denying misconduct, attacking the press and facing scrutiny about the competence of his inner circle of loyalists.

Through a former campaign spokesperson, Adams has released multiple statements in recent days clarifying that he had not profited off the token and had not moved investor funds, calling reports otherwise “false and unsupported by evidence.”

“Like many newly launched digital assets, the NYC Token experienced market volatility,” the spokesperson, Todd Shapiro, said Wednesday. “Mr. Adams has consistently emphasized transparency, accountability, and responsible innovation.”

A machine lawyer and an Israeli hotelier

Despite claims of transparency, Adams has so far declined to reveal his partners in the token.

But two people close to the project confirmed that Frank Carone, Adams’ former chief adviser and one-time lawyer for the Brooklyn Democratic Party, was closely involved in the launch. The two people spoke to The Associated Press on condition of anonymity because they had been asked not to disclose the identities of people involved in the token’s creation.

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One of Carone’s former clients, Yosef Sefi Zvieli, a real estate investor linked to several Israeli hotels, was also part of its creation, Shapiro confirmed to The Associated Press.

Zvieli, whose involvement was first reported by Business Insider, previously owned a college dorm in Brooklyn, which drew complaints from students of filthy conditions and neglect. After defaulting on his mortgage, Zvieli hired Carone as his attorney and was able to turn the troubled property into a city-financed homeless shelter.

Their exact role in the token launch was not immediately clear, though at least part of Zvieli’s job involved reaching out to influencers ahead of the debut. Neither he nor Carone appeared to have direct experience in cryptocurrency. Messages left with the two men were not returned.

As questions around the launch swirled this week, Adams sought guidance from Brock Pierce, the billionaire crypto investor, and former “Mighty Ducks” child actor, whose private jet he sometimes used as mayor.

After looking into the project, Pierce said he was confident that “no one has run off with anyone’s money.”

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Though he described himself as Adams’ “crypto adviser,” Pierce said he was only made aware of the project after its launch. “Had I been consulted, I would’ve put together a team of more qualified people who knew what they’re doing,” he added.

Political-coin instability

Even within the largely unregulated world of meme coins, experts say projects promoted by politicians are especially prone to unsavory trading practices.

The president of Argentina, Javier Milei, has faced fraud allegations for his own crypto promotion, which drew thousands of investors before swiftly collapsing. Coins launched by President Donald Trump and his wife, Melania Trump, also saw significant price fluctuations upon release.

The number of accounts that invested in NYC Token were far less than those ventures, totaling just over 4,000 as of Thursday, according to Nicolas Vaiman, the founder of Bubblemaps, which conducted an analysis of publicly available trade records.

Roughly 80% of those accounts had bought in during a 20-minute period before Adams had announced the coin but after it was made available for purchase, the analysis found. The window, Vaiman said, provided an advantage to insiders involved in the launch and other traders who pay close attention to new tokens.

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“Political coins are driven purely by attention, and the crypto community is aware that attention peaks right after the launch,” Vaiman said. “People know you don’t want to stick around, especially for such a vague prospect, like fighting anti-Americanism or antisemitism. What does it even mean? How are you going to achieve that in a token?”

The website for the coin says a “portion of the proceeds” will be divided evenly among three causes: antisemitism and anti-Americanism “awareness campaigns,” crypto education for the city’s youth and a scholarship initiative.

It does not detail which organizations will be supported, or what percentage of the proceeds will go toward charitable causes.

Uncertain fate

Adams has disputed that any money had been pulled by the token’s creators.

He has said the appearance of withdrawals were the result of adjustments made by the designated market maker, an entity that buys and sells orders of a new token to ensure traders can make purchases without major price shifts.

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The market makers include FalconX, a well known digital asset broker. The company declined to respond to inquiries on the record.

As of Wednesday, a majority of accounts that invested in the coin had lost money, according to the Bubblemaps analysis. Fifteen traders were down at least $100,000, while 10 had netted $100,000.

Pierce said he was still hoping the project could be salvaged, adding that “the fate and outcome of this project will be determined in the coming days.”

But some in the crypto world had their doubts.

“It could be a legitimate project with just a really bad rollout,” said Benjamin Cowen, the founder of another crypto research analytics firm, Into the Cryptoverse. “But the way it was launched didn’t instill a lot of confidence. It’s hard to regain trust in the crypto community.”

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Peter Schiff: Silver Is Running Out — Buy Now Before There’s Nothing Left

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Peter Schiff: Silver Is Running Out — Buy Now Before There’s Nothing Left
Silver’s surge to record highs is flashing urgent warnings about collapsing supply, mispriced mining stocks, and eroding currency confidence, with mounting volatility risks as prices race toward triple digits, economist Peter Schiff says.
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