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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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‘De-Worsified, Not Diversified’: Robert Kiyosaki Warns Investors on a Hidden Risk

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‘De-Worsified, Not Diversified’: Robert Kiyosaki Warns Investors on a Hidden Risk

Key Takeaways

Word Play With a Warning

Robert Kiyosaki, the author of the best-selling personal finance book “Rich Dad Poor Dad,” is recasting a familiar piece of investing advice. In a post on X, he argued that many investors only believe they are protected, adding:

“De-Worse-ified means they think they are diversified, but they have all their diversified assets, such as gold, silver, Bitcoin, stocks, bonds, real estate, and oil, in one asset class.”

His point is that spreading money across many holdings does not help if those holdings all move the same way in a crisis. When a liquidity shock hits, correlations rise and supposedly diverse portfolios can fall in unison, leaving investors “de-worsified” rather than diversified.

Image source: X

The commentary is consistent with the stance Kiyosaki has pushed throughout 2026 as he recently named bitcoin among the safest investments for the year, grouping it with what he calls real assets. He has repeatedly listed gold, silver, oil, food, bitcoin, and ether as his preferred holdings, framing them as scarce stores of value that printed money cannot dilute.

He has paired that view with stark price calls, setting a target of $250,000 for BTC by year’s end alongside a longer-term goal of $1 million. At current levels, the move would require a gain of more than 230%. On the precious metals side of things, he recently suggested a possible $200-per-ounce silver level this year, calling the metal’s climb a signal of mounting financial stress.

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Kiyosaki’s broader thesis is darker still, warning investors of a historic market crash that he ties to surging global debt and fragile private credit markets, urging followers to build income streams, learn trade skills, and accumulate hard assets before the storm.

Timing Is Everything

The “de-worsified” warning arrives at a tense moment for markets, especially as bitcoin posted its worst week since the 2022 collapse of Sam Bankman-Fried’s FTX exchange, sliding below $60,000 as record exchange-traded fund (ETF) outflows and risk-off sentiment gripped the sector.

That is exactly the kind of broad drawdown scenario (where bitcoin, equities, and other assets fall together) that Kiyosaki has used time and again to illustrate his point.

That said, he has become an increasingly polarizing voice within the broader economic landscape, with skeptics pointing out that his crash predictions are frequent and his price targets aggressive (and that he has issued similar warnings for years). Supporters argue his core message of owning scarce assets, avoiding hidden correlation, and preparing for volatility is a reasonable hedge against an era of heavy money printing and rising debt.

Whether or not his $250,000 bitcoin call lands, the distinction he is drawing is a real one, as true diversification really does depend on owning assets that behave differently (not simply owning many of them). In a market where everything from gold to crypto to stocks can move on the same macro headlines, that lesson may matter more than any single forecast.

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After hundreds of millions lost to fraud, NC lawmakers push for crypto ATM protections

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After hundreds of millions lost to fraud, NC lawmakers push for crypto ATM protections

North Carolina lawmakers on Tuesday advanced a bill to protect consumers from cryptocurrency kiosk fraud.

House Bill 920, which passed the House with a 115-to-0 vote, aims to regulate an industry that its author claims is unregulated in the state.

“It’s the wild, wild West,” Rep. Neal Jackson, R-Moore, said during a committee discussion on Tuesday. “There is no regulation whatsoever in North Carolina. That’s what we’re trying to do here.”

Lawmakers cited a growing amount of fraud as the reason for the bill. About $389 million in losses were reported last year through cryptocurrency ATMs, a 58% increase from 2024, according to the FBI. The majority of those impacted are 60-plus.

The bill now goes to the Senate for consideration. It seeks to:

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  • Require licenses for all kiosk operators under the Money Transmissions Act.
  • Place operators under the supervision of the Commissioner of Banks.
  • Require fraud warnings and transaction receipts for every transaction.
  • Require compliance and consumer protection officers that are always available.

It also seeks to place limitations on transactions in an effort to reduce fraud, requiring a $2,000 daily limit for the first 30 days for new customers and a $5,000 daily limit for existing customers, who would qualify after 30 days.

While other states have service fees between 20% and 30%, Jackson suggests putting a cap at 14%.

State Rep. Tim Longest, D-Wake, expressed concern about having the kiosks at all in the state. He said the bill’s protections could be stronger. 

“These machines can be the subject of fraud, basically facilitating fraud on seniors and other vulnerable individuals and in those cases,” Longest said. “… In crafting regulations, I think it’s important that we ensure consumers are adequately protected by those regulations and I do not believe that, under the language of the bill currently before you, those regulations are sufficient to protect consumers.”

Jackson pointed to this bill as an effort to regulate, not shut down, cryptocurrency kiosks in the state and said there are even more consumer protections in place.

David N. Tente, the executive director of the ATM Industry Association, said the bill — and others like it — is problematic because it requires operators to provide refunds to fraud victims in certain instances.  

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“In most cases, the cash in the ATM/kiosk does not belong to the operator, which means that returning any of it would be, technically, theft,” Tente said. “If you give someone cash for something, and you change your mind after they leave, you probably won’t get it back.”

He added: “We certainly feel sorry for those being scammed, but there are very simple things you can do to avoid it.”  

Tente said these kinds of scams have existed for centuries, adding: “They are still here — just using different means of payment.”

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Zcash Climbs 80% Since June 5 as Traders Shrug off Orchard Bug Fears

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Zcash Climbs 80% Since June 5 as Traders Shrug off Orchard Bug Fears

Key Takeaways

The Orchard Vulnerability

Privacy coin Zcash (ZEC) surged on Tuesday, jumping 11.3% to $478 as it maintained a steady recovery that began shortly after it plunged to just under $265. At the time of writing (5:32 a.m. EST), the privacy coin’s latest climb pushed its gains since June 5 to approximately 80% and saw ZEC’s market capitalization reclaim the $8 billion threshold.

The coin, alongside rival monero, was one of a handful of altcoins that logged gains exceeding 5% even as bitcoin dipped below the $63,000 threshold. ZEC’s surge above $470 on June 9 resulted in $11.5 million in short positions on the coin being wiped out in 24 hours, compared with $2.43 million in liquidated long bets.

While Zcash has since wrestled back its top-dog status from chief rival Monero, the asset is still trading at a steep discount compared to its pre-June 5 peak of just over $600. Before the correction, ZEC was riding a powerful wave of momentum, fueled by a resurgence in the crypto-privacy narrative and high-profile endorsements from industry heavyweights like Arthur Hayes. However, that bullish trajectory ground to a sudden halt. The catalyst for the reversal was the unsettling discovery of a critical vulnerability within Zcash’s Orchard shielded pool—a zero-knowledge security flaw that had quietly lay dormant since 2022.

Despite this, supporters of the privacy coin believe the uncovering of the bug has not damaged ZEC’s long-term appeal. Posting on X, Eunice Wong insisted there is an extremely low likelihood an exploit was executed and said traders who offloaded their holdings had overreacted.

“Long-term thesis hasn’t changed. In an AI-driven world where every transaction is tracked, financial privacy will become the scarcest asset, and ZEC is still one of the strongest privacy plays in crypto. Catching this falling knife is going to look like a genius move,” Wong wrote.

Matthew Brienen, managing partner at Cryptocharged, said while he recently reduced his ZEC holdings, it was purely a risk-management decision rather than a change in conviction. Nevertheless, he offered an explanation for why caution is warranted even if there is no proof that ZEC was counterfeited.

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“The Orchard bug isn’t a confirmed inflation event. It’s a confirmed inability to prove supply integrity. Those are not the same thing. The most important fundamental fact to remember is that turnstile accounting is not the same as proving Orchard balances are legitimate. You can track what entered. You can track what exited. That doesn’t prove every claim inside the pool was valid,” Brienen explained.

He added, however, that if counterfeit Orchard notes do exist, they could remain hidden until redemption is ultimately forced. According to Brienen, the recent price action suggests that is exactly what the market is trying to price in.

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