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Strategy Holders Might be at Risk From Michael Saylor’s Financial Wizardry

Is Strategy (MSTR) in trouble?
Led by Executive Chairman Michael Saylor, the firm formerly known as MicroStrategy has vacuumed up 506,137 bitcoin (BTC), currently worth roughly $44 billion at BTC’s current price near $87,000, in the span of about five years. To the casual observer, the company seems to have a magic, unlimited pool of funds from which to draw on to buy more bitcoin. But Strategy acquired a sizable chunk of its stash by issuing billions of dollars in equity and convertible notes (debt securities which can be converted into equity under special conditions), and more recently via the issuance of preferred stock, a type of equity that provides dividends to investors.
However, the price of bitcoin has been pushed down about 20% since peaking above $109,000 two months ago. And though such swings in prices are far from unusual, the particularly aggressive recent purchases by Saylor and team mean Strategy’s average acquisition price has risen to $66,000. The company is really only one more moderate swing down in price from being in the red on its buys.
Which begs the question: Could all of Strategy’s financial wizardry end up backfiring on the company should bitcoin keep heading lower?
“It’s highly unlikely that it results in a scenario where [Strategy] has to liquidate a bunch of bitcoin because it gets margin called,” Quinn Thompson, founder of crypto hedge fund Lekker Capital, told CoinDesk in an interview. “For the most part, the debt is very likely to be able to be refinanced for the convertible notes. And then [the firm] started issuing this perpetual preferred stock, which never has to be repaid.”
In other words, not only is there very little chance that Strategy could suffer the kind of blowup that shook over crypto firms and projects in 2022 (like Genesis or Three Arrows Capital), but the firm has even refrained from posting its bitcoin holdings as collateral for loans — with the exception of a loan taken from Silvergate, which was repaid in 2023.
Even so, that does not necessarily mean that it’s blue skies ahead for MSTR investors, because under various scenarios, Saylor could be forced to issue more equity than the market can handle in order to maintain course.
“If he’s not paying dividends with Strategy’s cash flow, he’s going to issue more shares and wreck the stock price. But it’s no different than what he’s doing already. Every time the retail bids it up, he wrecks the stock price by issuing more shares. In the future, he will have to do that, and the flows might not go into bitcoin. They might go to repay these debtors, and it will hurt the share price,” Thompson said.
Saylor’s balancing act
Strategy currently employs three different methods for raising capital: it can issue equity, convertible notes, or preferred stock.
Issuing equity means that Strategy creates new MSTR shares, sells them on the market, and uses the proceeds to buy bitcoin. Naturally, that creates selling pressure on MSTR and can potentially push the stock downward.
Convertible notes have allowed Strategy to raise funds quickly without diluting MSTR stock. Typically, investors like these notes because they offer a solid yield, they benefit if the stock surges, and they can usually be redeemed in cash for an amount equal to the original investment in addition to interest payments. The tremendous volatility of Strategy’s convertible notes, however, has allowed the company to mostly issue them at a zero percent interest rate and still meet high demand from sophisticated market participants, who have made bank trading that volatility.
Finally, Strategy has begun deploying preferred stocks. These are instruments that tend to appeal to investors seeking lower volatility and more predictable returns through dividends. There are currently two offerings: STRK, which gives an 8% annual return; and STRF, which pays 10% annualized.
But why is Strategy issuing all of these different types of investment vehicles? The idea is to create demand for Strategy for all kinds of investors that may have different tolerances to risk, Jeffrey Park, head of Alpha Strategies at crypto asset management Bitwise, told CoinDesk in an interview.
“The convertible bond investors and the common equity investors were generally aligned in that they were both volatility seeking structures,” Park said. “Preferred equities are different. They actually are favored by investors who want to minimize volatility at all costs for a steady, reliable and high coupon that they feel is worth the credit risk.”
“Strategy’s capital structure is almost like a seesaw in a playground,” Park added. “The common shareholders and converts are on one side, the preferred equity holders are on the other side. As sentiment shifts, the weights move around, and it tilts the value between these securities. But no matter how the seesaw moves, its total weight — which is Strategy’s enterprise value — remains the same. It’s just a redistribution of people’s perceived value across the liabilities that exist on the company’s balance sheet.”
Risks
Even so, Strategy now finds itself in a situation where it must pay 8% dividends on STRK, 10% dividends on STRF, and a blend of 0.4% interest rate on its convertible bonds.
With Strategy’s software business providing very little cash flow, finding the funds to pay for all of these dividends might be tricky.
The company will likely need to keep issuing MSTR stock to pay the interest it owes, Thompson said. “It will hurt the share price. In the most extreme scenario, the stock could trade at a discount [from its bitcoin holdings], because he would be having to issue shares to pay interest and cover cash flow.”
“The really draconian scenario would be for the discount to get so wide, like 20% or 30%, like Grayscale’s GBTC [prior to its conversion into an ETF], that the shareholders riot and tell him to buy back shares and close the discount,” Thompson added. “Right now, he’s adding shareholder value by selling the stock at an elevated price and buying bitcoin, but in the future the reverse might be true, where the best way to add shareholder value would be to sell the bitcoin and buy the stock. But that’s quite far away.”
Saylor lost controlling voting power over the company in 2024 due to the continuous issuance of MSTR stock, meaning that the scenario above could theoretically happen, especially if activist investors decided to get involved.
Another potential risk for MSTR holders is that the 2x long Strategy exchange-traded funds (ETFs) issued by T-Rex and Defiance, MSTX and MSTU, have seen weirdly persistent demand despite the stock’s drawdown. Every time investors want to gain or increase their exposure to these ETFs, the issuers have to buy twice as many MSTR shares. The popularity of these ETFs has helped create constant buying pressure for MSTR — so far, they’ve accumulated over $3 billion in MSTR exposure.
The problem is that the music might stop someday. And if these ETFs begin to sell off their MSTR shares, the reaction on the stock price could be violent.
“I don’t know where the endless capital comes from to buy the dip. These ETFs have gotten obliterated. They’re down huge,” Thompson said. “I mean, this is not a structural move up in the demand curve that you should count on. It’s not something you should really bake into your 10-year predictions of bitcoin price, but as long as it’s existing, it’s important for bitcoin. So I’m continually amazed by it.”
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StraitsX Launches Its Singapore-Dollar Pegged Stablecoin, XSGD, on XRP Ledger

Crypto infrastructure provider StraitsX debuted its Singapore dollar-pegged stablecoin, XSGD, on the XRP Ledger (XRPL) to cater to growing demand for regulated multi-chain stablecoins supporting real-time cross-border payments.
Digital asset developers, fintechs firms and financial institutions can use XSGD to conduct cross-border transactions, settle transactions on-chain and create programmable financial flows. XGSD is being powered by XRPL, a decentralized public blockchain from Ripple.
StraitsX, a major payment institution licensed by the Monetary Authority of Singapore, began issuing XSGD in 2020. The stablecoin pegged to the Singapore dollar is fully backed 1:1 by reserves held with DBS Bank and Standard Chartered.
As of writing, XSGD had a total supply of 14.12 million, with an onchain transaction count exceeding 8 billion. The stablecoin is available on Arbitrum, Avalanche, Ethereum, Polygon, Hedera and Zilliqa.
«At StraitsX, we’ve always approached stablecoins not just as digital representations of fiat, but as critical infrastructure for the future of financial markets. Launching XSGD on the XRP Ledger is a meaningful step toward that vision – an expansion of interoperability, programmability, and access across networks that were purpose-built for real-world value exchange,» Co-Founder and deputy of StaitsX, Liu Tianwei, told CoinDesk.
Regulated stablecoins like XSGD are better positioned to see increased adoption in the expected boom in cross-border economic activity in the coming years. For instance, per some estimates, cross-border e-commerce in Asia is expected to surpass $4 trillion by 2030. Meanwhile, global cross-border payments are projected to hit $250 trillion by 2027, according to a report published by Infosys Finacle last year.
The report mentioned Ripple while discussing various methods fintechs employ for money transfer. The report said that Ripple’s real-time settlement of funds «eliminates the need for pre-funding destination accounts and supports low-cost payments within seconds.»
Opening move
The debut of XSGD on the XRP Ledger marks the beginning of a series of upcoming rollouts outlined under the strategic partnership, the press release said.
In June, StraitsX plans to introduce a second phase focused on institutional applications, including programmable payouts, merchant settlements, and seamless compliance integrations for various financial workflows.
«StraitsX’s launch of XSGD on the XRP Ledger underscores that digital assets, including stablecoins, could play a pivotal role in payments» said Fiona Murray, managing director of APAC at Ripple.
«We are seeing a growing appetite for stablecoins like XSGD to support enterprise-grade use cases across payments, liquidity, and compliance-first infrastructure. Our collaboration with StraitsX to bring XSGD to the XRP Ledger supports our commitment to delivering regulated assets that can reshape cross-border payments and unlock value for financial institutions,» Murray added.
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Senate Dems Gear Up Resistance as Stablecoin Bill Meets Test Most Think Will Succeed

A key crypto bill has opened a rift among Senate Democrats as another big test approaches for the viability of legislation to regulate stablecoin issuers. Most expect the bill to clear a significant procedural vote on Monday night, but Democrats are split.
The Senate’s most prominent crypto critic, Massachusetts Democrat Elizabeth Warren, is leading a faction trying to dig in their heels on the bill, raising objections that include national security threats, consumer hazards and the corruption of a White House that’s conflicted because of President Donald Trump’s own digital assets business interests.
The other group, including Senator Kirsten Gillibrand, one of the bill’s primary backers, has argued that presidential conflicts are already illegal under the U.S. Constitution, and the bill doesn’t need to have specific constraints added to clarify that point. That side also praises a number of changes to the legislation to improve consumer protections and to partially address worries that large corporations will issue stablecoins — the steady, typically dollar-based tokens that underpin so much of the crypto markets’ transaction activity.
The bill is set for what’s known as a cloture vote on Monday night, which will decide whether it advances into a formal and time-limited period of debate before final consideration. Cloture tends to be the most difficult test for Senate legislation, because it requires 60 votes — much more than a simple majority. A previous version of the bill failed such a vote once before, when Democrats demanded more time to make changes.
The stablecoin bill is one of two highly significant U.S. legislative efforts that will finally establish a set of rules and system of oversight for crypto in the U.S., and many in the industry believe it’ll usher in a flood of interest from investors who’ve waited on the sidelines until the sector is completely regulated. The supporters of the stablecoin legislation have set it up for this vote, suggesting they were able to wrangle enough backers to triumph.
The current Senate bill — known as the Guiding and Establishing National Innovation for U.S. Stablecoins (GENIUS) Act — is worse than doing nothing, according to the arguments from the camp led by Warren, who is the ranking Democrat on the Senate Banking Committee. «A strong bill would ensure that consumers enjoy the same consumer protections when using stablecoins as they do when using other payment systems, close loopholes that enable the illicit use of stablecoins by cartels, terrorists, and criminals, and reduce the risk that stablecoins take down our financial system,» according to a sheet issued on Monday by the committee’s Democratic staff. «The GENIUS Act does not meet those minimum standards.»
Gillibrand, however, said the bill has been written in a «truly bipartisan effort.»
«Stablecoins are already playing an important role in the global economy, and it is essential that the U.S. enact legislation that protects consumers, while also enabling responsible innovations,” the New York Democrat said in a statement last week.
Senator Mark Warner, a Virginia Democrat, also explained his view in choosing to support the bill. “It sets high standards for issuers, limits big tech overreach and creates a safer, more transparent framework for digital assets,» he said in a statement. «It’s not perfect, but it’s far better than the status quo.”
Read More: U.S. Stablecoin Bill Could Clear Senate Next Week, Proponents Say
In the hours before the planned Monday vote, a coalition of 46 consumer, labor and advocacy groups continued objecting to the legislation, which has been overhauled repeatedly.
«A vote for this legislation would enable and condone cryptobusiness activities by the Trump administration, organization, and family that raise unprecedented concerns about presidential conflicts of interest, corruption, and the abuse of public office for private gain,» they wrote in a letter to the Senate leadership.
The crypto industry itself has come together to support the legislation, with various lobbyist groups publishing statements arguing lawmakers should advance the legislation. Stand With Crypto, a Coinbase-backed group focused on getting voters to support crypto issues, warned lawmakers in a statement Monday that their votes would go into its sometimes arbitrary assignment of grades for politicians’ crypto sentiment.
While the stablecoin bill has drawn some political heat, it’s widely expected to be the easier of the two crypto efforts on Capitol Hill. The legislation to establish U.S. market rules for crypto is much more complex. For both bills, the House of Representatives is also working on parallel efforts.
If the bill clears cloture, it could speed toward Senate passage in a matter of days. Jaret Seiberg, a policy analyst with TD Cowen, expects it to clear the Senate this week
“That means it could become law by summer as we see the House moving quickly on the bill,” he wrote in a note to clients.
Warren wrote her own letter on Monday to the U.S. Department of the Treasury and the Department of Justice, pressing for answers about what’s being done about North Korean hackers who stole more than a billion dollars in assets from exchange Bybit earlier this year.
«These stolen assets have helped keep the regime afloat and supported continued investments in its nuclear and conventional weapons programs,» Warren and Senator Jack Reed, a Rhode Island Democrat, wrote to the Treasury secretary and attorney general. «Reports suggest there are potentially thousands of North Korean-affiliated crypto hackers around the globe.”
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Bitcoin Climbs to $105K; Crypto ETF Issuer Sees 35% Upside

Cryptocurrencies regained footing on Monday after a rocky start to the trading session, mirroring a broader recovery in risk assets as traders digested Moody’s downgrade of U.S. government bonds.
Bitcoin BTC notched a strong rebound after slipping to as low as $102,000 early in the U.S. session, following its record weekly close at $106,600 overnight. The largest cryptocurrency by market cap climbed back to $105,000 in afternoon trading, up 0.4% over 24 hours. Ether ETH rose 1.2%, reclaiming the $2,500 level.
DeFi lending platform Aave AAVE outperformed most large-cap altcoins, while the majority of the broad-market CoinDesk 20 Index members still remained in the red despite advancing from their daily lows. Solana SOL, Avalanche AVAX and Polkadot DOT were down 2%-3%.
The bounce extended to U.S. stocks, too, with the S&P 500 and Nasdaq erasing their morning decline.
The early pullback in crypto and stocks came after Moody’s late Friday downgraded the U.S. credit rating from its AAA status. The move rattled bond markets, pushing 30-year Treasury yields above 5% and the 10-year note to over 4.5%.
Still, some analysts downplayed the downgrade’s long-term impact on asset prices.
«What does [the downgrade] mean for markets? Longer-term – really nothing,» said Ram Ahluwalia, CEO of wealth management firm Lumida Wealth. He added that in the short term there might be some selling pressure centered on U.S. Treasuries due to large institutional investors rebalancing, as some of them are mandated to hold assets only in AAA-rated securities.
«Moody’s is the last of the three major rating agencies to downgrade U.S. debt. This was the opposite of a surprise – it was a long time coming,» Callie Cox, chief market strategist at Ritholtz Wealth Management, said in an X post. «That’s why stock investors don’t seem to care.»
Bitcoin targets $138K this year
While BTC hovers just below its January record prices, digital asset ETF issuer 21Shares sees more upside for this year.
«Bitcoin is on the verge of a breakout,» research strategist Matt Mena wrote in a Monday report. He argued that BTC’s current rally is driven not by retail mania, but by a confluence of structural forces, including institutional inflows, a historic supply crunch and improving macro conditions that suggests a more durable and mature path to fresh all-time highs.
Spot Bitcoin ETFs have consistently absorbed more BTC than is mined daily, tightening supply while major institutions, corporations such as Strategy and newcomer Twenty One Capital accumulate and even states explore creating strategic reserves.
These factors combined could lift BTC to $138,500 this year, Mena forecasted, translating to a roughly 35% rally for the largest crypto.
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