Connect with us

Finance

MicroStrategy’s ‘financial engineering’ powers ascent to Nasdaq 100

Published

on

MicroStrategy’s ‘financial engineering’ powers ascent to Nasdaq 100

MicroStrategy has raised almost $20bn from investors this year to buy bitcoin, fuelling a meteoric rise for the once-obscure software company into the Nasdaq 100 index of large-cap US technology stocks.

A combination of selling shares and convertible bonds has funded a one-way bet on a rocketing bitcoin price that, despite a sell-off in recent days, has driven its shares up more than 400 per cent this year. Such is the investor demand that the company now has a market value of around $80bn, despite owning around $41bn of bitcoin.

Debt fund managers have been clamouring to get their hands on the convertible bonds, believing they offer exposure to the soaring share price while also providing protection if the price goes into reverse. The stock’s Nasdaq 100 inclusion will compel index-tracking funds to buy billions of dollars more of the company’s shares.

Its index inclusion after the close of trading on Friday — it is part of a trio replacing IT firm Super Micro Computer, Covid-19 vaccine maker Moderna and gene-sequencing company Illumina — is further vindication for founder Michael Saylor, who has become one of the most evangelistic proponents of bitcoin since his company began buying it four years ago.

“It’s some incredible financial engineering,” said a convertible bond portfolio manager invested in MicroStrategy. “[Saylor has] created this incredible situation where a stock trades at three times the price of the underlying bitcoin and then he just sells more shares every day and buys more bitcoin.”

Advertisement
Donald Trump has promised to make the US a ‘bitcoin superpower’ and ease the regulatory crackdown on cryptocurrency © Justin Chin/Bloomberg

For Saylor, who once tweeted that bitcoin’s “days are numbered” but later recanted, this year has been an extended opportunity to build on his plan to make MicroStrategy a “treasury” for what he calls “the most valuable asset in the world”. In October he announced plans to raise $42bn over the next three years, all to pay for more bitcoin.

The cryptocurrency’s value has more than doubled this year following the arrival of spot bitcoin exchange traded funds in the US and Donald Trump’s presidential election victory in November. Trump’s promises to make the US a “bitcoin superpower” and ease the regulatory crackdown pushed the value of the coin from less than $64,000 at the end of September to more than $108,000 this week, although at one point on Friday it fell close to $92,000.

“My attitude [on bitcoin] has gotten better every quarter,” Saylor told the Financial Times. “Now you have a president[-elect] who is ending the war on crypto.”

MicroStrategy’s success has been helped by the huge premium that investors place on its shares, with the company currently trading at roughly double the net asset value of its bitcoin holdings.

This allows it to issue stock at a premium and buy ever more of the cryptocurrency. Although existing shareholders end up owning a smaller percentage of the company, the underlying value of their shares increases because MicroStrategy now owns more bitcoin per share.

Advertisement
Line chart of Share price, $ showing MicroStrategy shares have climbed 370% this year

Convertible bonds have also become a key way for MicroStrategy to raise money. Such instruments usually pay a fixed coupon but also convert into shares at an agreed price, allowing investors to benefit from equity’s unlimited upside while providing the perceived downside protection of bonds.

The highly volatile nature of the stock has so far worked well for both the company and investors. It means the company can issue bonds with a higher conversion premium than usual and even offer zero coupon on the debt. Investors, meanwhile, have been drawn to the potential exposure to the firm’s soaring share price and the perceived downside protection.

As MicroStrategy’s shares surged earlier this year, bond investors who had lapped up its March convertibles quickly became equity holders as their bonds were converted. In November, Saylor returned to market for the fifth time this year, issuing $3bn of convertibles for zero interest and a 55 per cent conversion premium.

MicroStrategy Inc. headquarters in Tysons Corner, Virginia,
‘It’s arbitrage feeding arbitrage,’ said one convertible bond trader who has bought MicroStrategy’s bonds and shorted its equity © Stefani Reynolds/Bloomberg

For investors who had snapped up MicroStrategy’s earlier debt, the company’s return to market could hardly have worked out better, as it allowed them to take profits on their shares and buy new bonds.

“This was an absolute home run for us. We got to lock in all of the upside of the past six months, and now we bring in downside protection,” said one convertible bond fund manager who owns MicroStrategy bonds. “There is no better outcome for a convertible bond manager.”

So-called convertible arbitrage hedge funds, which buy such bonds and then short the shares — bet on a falling price — have also provided a ready market for the firm’s mass issuance.

Their strategy is essentially a bet on volatility. They try to make money on their short position if the share price falls, with losses on the convertible limited by the bond’s downside protection. And if the shares climb, the aim is for the short position — which is smaller than the convertible bond exposure — to lose less money than the gain on the equity upside.

Advertisement

“It’s arbitrage feeding arbitrage,” said one convertible bond trader who has bought MicroStrategy’s bonds and shorted its equity. “Our arbitrage is OK. It’s decent. But [Saylor’s] arbitrage is brilliant.”

Traders exploiting the volatility of MicroStrategy’s shares have been helped by billions of dollars of inflows into highly levered exchange traded products that track the stock but amplify investors’ potential gains and losses. Two MicroStrategy ETFs, including the Defiance Daily Target two-times long MSTR ETF, own about $10bn of the company’s stock via swaps and options. 

Unlike traditional ETFs, which buy and hold shares, leveraged ETFs rebalance at the end of every trading day to hit their targeted returns. This means that when the underlying asset rises in price, fund managers must buy more of the stock, and vice versa should prices fall.

These end-of-day rebalancing flows can “significantly impact the underlying MicroStrategy stock price, amplifying price moves, thus enhancing volatility”, said JPMorgan strategist Nikolaos Panigirtzoglou.

But some investors are getting nervous. They fear that the virtuous circle that has driven up the share price so quickly could easily go into reverse if the bitcoin price falls substantially.

Advertisement

“Borrowing dollars to buy bitcoin is just a massive dollar short position, not a new financial invention,” says Barry Bannister, chief equity strategist at Stifel. “As any short seller in history knows, the price of being wrong is ruin.”

“If bitcoin traded down 90-95 per cent and stayed there, there would be no liquidation or debt accelerations,” Saylor told the FT. “Presumably our equity would suffer some dilution, but we still would not sell, or need to sell, our bitcoin.”

The shares could also fall if investors simply decide to place less of a premium on MicroStrategy stock. Since their peak on November 21, the shares are down around 40 per cent, while bitcoin is down just 5 per cent.

One North American hedge fund executive said they had held a position in bitcoin and a bet against MicroStrategy “to capture that spread”. This bet “worked on and off until the trade became a meme”, added the person, who now prefers to short one of the twice-leveraged ETFs.

Some suggest that share sales by insiders undermine the company’s pitch to investors: that bitcoin remains undervalued. MicroStrategy directors have sold a total of $570mn of the company’s stock so far this year, according to company filings.

Advertisement

MicroStrategy did not respond to a request for comment on the share sales.

Some content could not load. Check your internet connection or browser settings.

“The subjects change — now it’s crypto — but over the centuries human investment behaviour does not deviate from the script one iota,” said Bannister.

Anyone buying assets “built on thin air” should be prepared to watch their money “vanish”, he added.

Continue Reading
Click to comment

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Finance

Block vs. PayPal: Which Fintech Stock Is Better Positioned for 2026? | The Motley Fool

Published

on

Block vs. PayPal: Which Fintech Stock Is Better Positioned for 2026? | The Motley Fool

Two companies battling to win the global payments market.

Great businesses win by solving problems, and the $2.5 trillion global payments market is a goldmine for companies that can make money move effortlessly.

Two of the firms competing in that space are Block Inc. (XYZ +4.85%) and PayPal Holdings Inc. (PYPL +1.30%).

Image source: Getty Images.

As each pushes into new technologies and revenue streams, the next year could define their long-term trajectories.

Advertisement

With this potential turning point, I’ll examine which fintech stock may fit best in your portfolio.

PayPal’s moves into AI, global payments, and stablecoins

PayPal shares have dipped 37.28% over the last year, but the company has three initiatives that could help reverse that trend: PayPal World, artificial intelligence (AI) agents, and cryptocurrencies and stablecoins. PayPal World and AI agents enhance the current services, while crypto and stablecoins open up entirely new financial terrain for PayPal.

PayPal Stock Quote

Today’s Change

(1.30%) $0.52

Current Price

$40.42

Advertisement

Announced in June 2025, PayPal World will allow customers to pay global merchants using their payment system, or wallet of choice, in their local currency. In essence, you’ll start seeing PayPal integrate seamlessly with other payment services.

Advertisement

For AI shopping, PayPal says a customer can tell an AI agent they need a ride to the airport at 4:50 a.m. The agent can both book that appointment and pay for it.

Finally, that brings us to cryptocurrencies and stablecoins. The company enables the buying, selling, and sending of crypto within its wallets. PayPal also offers its own stablecoin pegged to the U.S. dollar called PayPal USD (PYUSD) for fast, global payments. As of this writing, holding PYUSD offers a 4% annual yield.

Its peer-to-peer payment service, Venmo, can also boost revenue over time. As a reference point, in 2021, PayPal said it generated roughly $900 million from Venmo. PayPal expects it to generate $2 billion in revenue by 2027.

Block’s next growth chapter

Similar to PayPal, Block shares have stumbled over the last year, dipping 22.48%.

Block Stock Quote

Today’s Change

(4.85%) $2.59

Advertisement

Current Price

$55.97

Once again, the key is looking at what lies ahead.

Advertisement

Its flagship Cash App service still has the reputation of friends just sending each other money, but Block is focused on turning it into a complete financial platform. Through banking, savings, direct deposit, bill paying, an AI-powered money assistant, and more, users are gaining fuller control of their financial lives through just one app. In Q3 2025, Block reported $1.62 billion in gross profit from Cash App, a 24% year-over-year increase.

Its global lending products have now surpassed $200 billion in provided credit. Defaults remain low, with 96% of buy now, pay later installments paid on time and 98% of purchases incurring no late fees.

Outside of its consumer products, Block is building out a robust suite of merchant tools to provide businesses with everything they may need, including credit card terminals, payroll services, and loyalty program marketing campaigns. Business owners can also build websites through Block, which could lead sellers to adopt more of its tools over time.

Block has also leaned deeper into cryptocurrencies. In October 2025, it launched Square Bitcoin, which will automatically convert credit card sales into Bitcoin. Block also holds roughly 8,800 BTC, worth nearly $770 million.

The PayPal vs. Block winner

PayPal and Block are both stocks that could rebound in 2026 if their initiatives gain traction.

Advertisement

Block has high-growth segments in cryptocurrencies and lending, and its expanding suite of services and tools for businesses can help it generate more revenue from its current customer base. That high upside potential also comes with a high beta of 2.66, meaning it is more than two and a half times more volatile than the general stock market. Despite those issues, the balance sheet is strong, with $8.7 billion in cash compared to $8.1 billion of debt.

PayPal has steady, transaction-based fees from its global payments platforms and even pays out a dividend of $0.56 per share. Its beta of 1.43 also means it’s less volatile than XYZ. This may appeal more to risk-averse investors. The key here will be if PayPal’s recent moves can take it beyond being just a steady and mature business. With $12.17 billion in debt and $10.76 billion in cash, PayPal operates with a slight net debt that’s reasonable considering its consistent earnings.

Ultimately, the choice comes down to whether you prefer owning PayPal as a dependable revenue machine that could grow meaningfully as it enhances its services and features, or Block’s higher-risk path that could deliver outsized returns if its bets pay off.

Continue Reading

Finance

Bond Markets Are Now Battlefields

Published

on

Bond Markets Are Now Battlefields

As the Greenland crisis came to a head in the days before Davos, Europeans sought tools that could be reforged as weapons against the Trump administration. On Jan. 18, Deutsche Bank’s global head of foreign exchange research, George Saravelos, warned clients in a note that “Europe owns Greenland, it also owns a lot of [U.S.] treasuries,” and that the EU might escalate the conflict with a “weaponization of capital” by reducing private and public holdings of U.S. debt instruments.

U.S. Treasury Secretary Scott Bessent reported later that week that Deutsche Bank no longer stood behind the analyst’s report, but Saravelos was far from the only financial analyst to discuss the idea. Within days, a few European pension funds eliminated or greatly reduced their holdings of U.S. Treasurys and—perhaps as a result—U.S. language about European strength became considerably less aggressive.

As the Greenland crisis came to a head in the days before Davos, Europeans sought tools that could be reforged as weapons against the Trump administration. On Jan. 18, Deutsche Bank’s global head of foreign exchange research, George Saravelos, warned clients in a note that “Europe owns Greenland, it also owns a lot of [U.S.] treasuries,” and that the EU might escalate the conflict with a “weaponization of capital” by reducing private and public holdings of U.S. debt instruments.

U.S. Treasury Secretary Scott Bessent reported later that week that Deutsche Bank no longer stood behind the analyst’s report, but Saravelos was far from the only financial analyst to discuss the idea. Within days, a few European pension funds eliminated or greatly reduced their holdings of U.S. Treasurys and—perhaps as a result—U.S. language about European strength became considerably less aggressive.

Advertisement

It’s unclear how much of an impact Europe’s moves had on the White House backing off. But it poses a number of questions: Can Europe take advantage of weaponized interdependence to wage financial warfare against the United States? How big are the obstacles in the way, and how much impact can such moves have?

Financial flows and financial policy are instruments of coercive power. There is some evidence of financial flows putting pressure on the United States last year; in the wake of his triumphant declaration of mass tariffs in April, movement away from Treasurys reportedly persuaded President Donald Trump to partly change course.

However, this seems to have been an organic, unplanned development and a short-lived one.

Despite the precipitous fall of the dollar, and lively discussion over the past year of the United States losing its reserve currency status, the evidence points to mundane concerns about inflation and policy uncertainty leading to a slow reallocation of investment from the United States to other countries rather than any kind of coordinated response. Expert observers have asked if it is even possible for Europe to do anything further given its active trade with the United States, its smaller markets, and its interdependence. The Financial Times’s Alphaville blog summarized the idea of weaponization as “implausible.”

Yet the potential is there. History can be instructive. The state weaponization of finance feels new but, in fact, is centuries old. In the last decades of the 19th century, European governments—particularly France and Germany—aggressively used finance to advance their interests. The subservience of finance to diplomacy was considered natural; to propose otherwise could be dismissed as “financial pacifism.” At a critical moment in conflict with Russia, German Chancellor Otto von Bismarck banned the Reichsbank from accepting Russian securities as collateral. After the Franco-Prussian War an “official but tacit ban” was used to prevent French investors from putting any money into Germany.

Advertisement

How might similar action look today?

The main battlefield for weaponization is markets for sovereign debt—Treasurys on the U.S. side and the mix of national and European Union-level debt instruments on the European side. If Carl von Clausewitz had been a banker instead of a general, he would have pointed to these instruments as the “center of gravity” of any coercive financial operations. Here, the United States has a distinct advantage: Treasurys are the core market of international finance—large, very deep, very liquid. They form the backbone of world financial flows, a major channel of supply and demand for local markets everywhere.

Virtually all national financial markets are tied to the U.S. Treasury market, and it greatly eases the U.S. ability to borrow. This makes it a potentially powerful target for European pressure but also, at best, a delicate one—it is very difficult to launch pressure that does not boomerang back against the EU. Much of EU ownership of Treasurys is also in private hands.

Despite all this, European governments still have the means to go on the offensive. Finance is notoriously sensitive to the arbitrage opportunities created by regulation, such that leading textbooks on the industry include extensive discussion of loophole mining. (This may also explain why lawyers can now earn more than bankers on Wall Street.) If clever bureaucrats at the European Central Bank and EU and elsewhere created the right loopholes, then European funds could move accordingly. Instead of banning use of Treasurys as collateral à la Bismarck, slight adjustments of their risk weight or tax impact under EU or national law should do the trick. There are great technical and political challenges, but it is absolutely doable.

On a defensive basis, Europe can improve its financial position by further developing common  EU debt, building on the large-scale Next Generation EU issuance during the COVID-19 pandemic. In December, EU leaders agreed to raise 90 billion euros ($106.3 billion) for Ukrainian defense, and further steps are very much under discussion. The political and technical challenges to full development of common debt options are obviously enormous, requiring the historically unprecedented establishment of a large, stable market for supranational debt.

Advertisement

EU common debt tends to trade at a discount relative to comparable national debt, showing investors’ concerns. However, the potential payoffs are significant. In addition to facilitating EU-wide defense planning and creating a clear substitute for the Treasurys market, a strong common debt market could create a new and more powerful backbone to European finance, investment, and economic growth.

None of the above analysis should be viewed as prescriptive; by far the best path forward is a negotiated return to the rules-based order as opposed to a collapse into the full anarchy of unrestrained interstate competition. Unfortunately, the Trump administration seems committed to an aggressive policy that puts that order in peril. From at least the Napoleonic wars to the end of World War II, national interests regularly hijacked international markets, pushing them away from their idealized Economics 101 role as mechanisms of price discovery and efficient allocation into channels of pressure and coercion.

In an effort to bottle up these destructive spirits, the Franklin Roosevelt administration—with the assistance of economist John Maynard Keynes—used the United States’ status as the most powerful surviving state to implement the Bretton Woods system of financial and political controls. The success of the Bretton Woods project can be measured in part by how many of the tactics of the previous eras have been forgotten.

As the past month shows, these tactics and their destructive side effects are reemerging as the order collapses. Once again, bond markets are now battlefields.

Advertisement
Continue Reading

Finance

State finance committee approves bill to fund homeless veterans support

Published

on

State finance committee approves bill to fund homeless veterans support

People working to support homeless veterans say a bill advancing in the state Capitol would provide much needed funding. But they also say it doesn’t address a housing need outside of southeastern Wisconsin. 

This week, the Legislature’s Joint Finance Committee unanimously approved funding for the bill, which would provide $1.9 million spread out in $25 per diem payments to nonprofits that house veterans. 

Greg Fritsch is president of the Center for Veterans Issues, a Milwaukee-based nonprofit that provides housing and supportive services for veterans throughout the state. Fritsch told WPR’s “Wisconsin Today” that the bill is a step in the right direction.

News with a little more humanity

WPR’s “Wisconsin Today” newsletter keeps you connected to the state you love without feeling overwhelmed. No paywall. No agenda. No corporate filter.

Advertisement

“It’s not enough, but it will go a long way,” he said. 

Besides safe housing, the Center for Veterans Issues program offers support programs and meals to veterans. Fritsch said his group typically operates on a yearly $500,000 deficit, which the bill’s funding would help alleviate. 

“Costs never stop going up,” he said. “This will go a long way to helping us provide more beds to veterans.”

Fritsch said his program currently houses 81 men and five women in sites around southeastern Wisconsin. 

Advertisement

Currently, the federal Department of Veterans Affairs provides about $85 in per diem payments to nonprofit veterans support organizations for housing and care.  

While Fritsch said his organization provides some services like rental assistance statewide, its transitional housing work is only happening in southeastern Wisconsin.

Joey Hoey, assistant deputy secretary at the Wisconsin Department of Veterans Affairs, told “Wisconsin Today” there is clearly a problem in finding safe housing for veterans, and funding is part of that problem.

Hoey said the $85 per diem payments from the federal VA “is barely enough to house (veterans), let alone provide the kind of counseling and education to get people back on their feet.”

In September of last year, the state VA closed two of its Veteran Housing and Recovery Program facilities, one based in Chippewa Falls and the other in Green Bay. 

Advertisement

The bill advanced by the finance committee would not provide the state VA with money to reopen the centers. Instead, it goes toward nonprofit programs which are currently based in southeastern Wisconsin, according to Hoey. 

“We fully support these nonprofits — they’re our partners and they do great work. But they’re in Madison, Janesville and Milwaukee,” he said. “It means that none of this money is going to help, no matter what some might try and tell you. This money is not going to help homeless veterans in the northern and western parts of the state.” 

Hoey said he previously warned lawmakers the closures of state facilities in northern Wisconsin would happen without proper funding in the state budget. The compromise budget between Democratic Gov. Tony Evers and the Republican-controlled Legislature didn’t include funding for the state VA facilities. 

“The Joint Finance Committee did this knowing full well that we would have to close those two facilities,” Hoey said. “When the Legislature voted the final vote and didn’t put that money back in the budget, we had to make the tough decision to figure out how much money we had, and we could only keep one of the sites open.” 

The state VA still operates a veterans care facility in Union Grove in southeastern Wisconsin. 

Advertisement
Continue Reading

Trending