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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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Institutional Crypto Adoption ‘Happening Now’: Ripple Executive Says Real-World Use Cases Taking Hold

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Institutional Crypto Adoption ‘Happening Now’: Ripple Executive Says Real-World Use Cases Taking Hold

Key Takeaways:

  • Ripple says institutional adoption of digital assets is happening now.
  • Craddock states the focus has shifted to infrastructure and real-world use cases.
  • Paris events showed strong momentum, with Ripple citing real industry energy.

Institutional Digital Asset Adoption Gains Momentum

Institutional adoption of digital assets is gaining momentum across global finance, marking a decisive shift as major firms move beyond experimentation into active deployment. Ripple’s managing director for the U.K. and Europe, Cassie Craddock, reinforced this momentum on April 20, pointing to Paris Blockchain Week 2026 and related industry events as evidence that large-scale crypto adoption is already underway.

Craddock stated on social media platform X:

“Institutional adoption of digital assets isn’t something that’s on the horizon. It’s happening now.”

“The debate has moved on. The focus is on infrastructure and real-world use cases. And the people I was fortunate enough to spend time with this week are the ones building it. Banks, asset managers, fintechs, and regulators, all discussing how to do this properly and at scale,” she further shared.

The executive tied that view to meetings held across the Ripple Roadshow Paris, Paris Blockchain Week itself, Mastercard Crypto Day at the Eiffel Tower, and Société Générale-FORGE’s event at the French Ministry of Finance. She explained that discussions no longer centered on whether institutions would engage with the sector. Instead, participants examined infrastructure, deployment standards, and real-world use cases that could support broader activity across regulated financial markets.

Paris Events Highlight Structured Industry Buildout

The comments suggest that digital asset conversations among large organizations are becoming more operational. Craddock referenced exchanges with speakers including David Durouchoux, Myles Harrison, and Frédéric Dalibard, while also highlighting the presence of banks, asset managers, fintechs, and regulators. That mix suggests several parts of the financial system are considering similar questions around scale and execution. Rather than focusing on abstract potential, the gatherings in Paris appeared to center on how institutions can build and apply digital asset systems in a structured way.

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The Ripple executive added that the people involved in those meetings are “the ones building it.” She also concluded:

“The energy was real, the momentum even more so.”

These remarks reflect Ripple’s view that institutional interest is moving from long-term expectation to active development. By stressing implementation and participation from established financial groups, the post framed Paris Blockchain Week as a signal that digital asset adoption is advancing within mainstream finance.

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Scattered Spider hacker pleads guilty to stealing $8 million in cryptocurrency – Help Net Security

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Scattered Spider hacker pleads guilty to stealing  million in cryptocurrency – Help Net Security

A British national tied to the Scattered Spider cybercrime group pleaded guilty to hacking multiple companies via SMS phishing and stealing over $8 million in virtual currency from US victims.

Tyler Robert Buchanan, 24, of Dundee, Scotland, pleaded guilty to conspiracy to commit wire fraud and aggravated identity theft.

In November 2024, US authorities unsealed criminal charges against Buchanan and four other alleged members of the Scattered Spider group, accusing them of using phishing text messages to steal employee credentials, breach company systems and steal cryptocurrency.

According to court documents, Buchanan and his co-conspirators conducted cyber intrusions and virtual currency thefts between September 2021 and April 2023.

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The victims included interactive entertainment, telecommunications and technology companies, as well as business process outsourcing (BPO) and IT service providers, cloud communications firms, virtual currency companies and individual victims.

“As part of the scheme, Buchanan and his co-conspirators conducted Short Message Service (SMS) phishing attacks by sending hundreds of SMS phishing messages to the mobile telephones of a victim company’s employees. The messages purported to be from the victim company or a contracted IT or BPO supplier for the victim company,” the Justice Department said.

“The SMS phishing messages contained links to phishing websites designed to look like legitimate websites of a victim company or a contracted IT or BPO supplier. The websites then lured the recipient into providing confidential information, including personal identifying information (PII), and account usernames and passwords.”

In April 2023, police found on a digital device at Buchanan’s residence in Scotland the names and addresses of numerous victims, including a text file containing cryptocurrency seed phrases and login credentials for one account.

Buchanan has been in federal custody since April 2025 and faces up to 22 years in federal prison.

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Co-conspirator Noah Michael Urban is serving a 10-year federal prison sentence and was ordered to pay $13 million in restitution after pleading guilty in April 2025 to fraud-related charges. Three other defendants charged alongside Buchanan, including Ahmed Hossam Eldin Elbadawy, Evans Onyeaka Osiebo and Joel Martin Evans, still face criminal charges in the case.

Scattered Spider is a cybercrime collective, also known as UNC3944, Muddled Libra and Octo Tempest, made up largely of young, native English-speaking hackers who use social engineering, including impersonating IT and help-desk staff, to gain initial access, bypass MFA, and compromise enterprise networks.

The group gained notoriety for its role in high-profile hacking and extortion attacks against Caesars Entertainment and MGM Resorts International, two of the largest casino operators in the US.

Although authorities have increased pressure on the group and arrested several members, including four they consider responsible for ransomware attacks targeting UK-based retailers last year, the group continues to operate, with new members replacing those arrested.

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XRP Prepares for Quantum Future as Ripple Maps XRPL Strategy for Security Readiness

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XRP Prepares for Quantum Future as Ripple Maps XRPL Strategy for Security Readiness

Key Takeaways:

  • Ripple outlines a phased roadmap to prepare XRPL for quantum-era cryptography risks.
  • Industry momentum grows as XRPL testing highlights performance and security tradeoffs.
  • Developers at Ripple will expand testing to balance innovation with network stability.

Ripple Maps Quantum Security Strategy

Ripple’s post-quantum strategy reflects a growing shift in blockchain security as quantum computing risks gain credibility. The company’s latest Insight, published April 20 by Senior Director of Engineering Ayo Akinyele, outlined a structured roadmap to prepare the XRP Ledger for future cryptographic disruption while preserving network performance.

The Insight stated:

“Ripple is introducing a multi-phase roadmap to prepare the XRP Ledger (XRPL) for a post-quantum future, with a target for full readiness by 2028.”

It also detailed collaboration efforts: “Ripple is working with Project Eleven to accelerate development, including validator testing and early custody prototypes.”

Akinyele explained that quantum security is becoming more relevant because blockchain networks rely on cryptographic systems that could eventually be broken by sufficiently advanced quantum computers. On XRPL, each signed transaction reveals a public key on-chain, which could weaken long-term wallet security in a post-quantum environment.

He also pointed to the “harvest now, decrypt later” threat, where attackers collect cryptographic data today and wait for future quantum capabilities to exploit it. While this does not indicate an immediate failure of current protections, it increases the urgency of preparing systems that secure long-duration value. These risks reinforce the need for early testing of quantum-resistant cryptographic systems and structured migration planning.

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XRPL Testing Targets Long-Term Stability

Ripple’s roadmap consists of four phases, starting with contingency planning for a potential failure of existing cryptographic standards. This includes a “Quantum-Day” framework designed to enable secure migration to post-quantum accounts if vulnerabilities emerge. Additional phases focus on evaluating National Institute of Standards and Technology (NIST)-recommended algorithms under real network conditions, measuring impacts on throughput, storage, and verification efficiency. XRPL’s native features, including key rotation and deterministic key generation, provide a technical advantage by enabling gradual migration without forcing users to abandon existing accounts. Parallel testing on development networks will allow developers to assess performance tradeoffs before broader implementation.

The senior director of engineering emphasized long-term execution and coordination, stating:

“We should not view addressing the quantum threat on XRPL as a single upgrade, but rather a multi-phased strategy of carefully migrating a live, global financial infrastructure without compromising the value of digital assets protected by the XRPL.”

Akinyele indicated that achieving post-quantum readiness requires balancing cryptographic innovation with operational stability, ensuring the network remains efficient while adapting to future security challenges.

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