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

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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.”

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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.

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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.

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“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.

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“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.

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

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“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.

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Auto Finance Capital Summit | Insights | Mayer Brown

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Auto Finance Capital Summit | Insights | Mayer Brown

Stuart Litwin will be speaking at the Auto Finance Capital Summit taking place May 11-12 in Nashville, TN. This event brings together capital markets, finance, and treasury leaders across the $1.5 trillion auto finance industry to tackle critical funding challenges — from securitization and warehouse lending to liquidity management, private credit, and capital efficiency.

For more information about the event, please visit the event page.

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Yes, retail investment needs a boost – but the squirrel looks too tame | Nils Pratley

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Yes, retail investment needs a boost – but the squirrel looks too tame | Nils Pratley

Red squirrel characters have a history in the public information game. Older UK readers may recall Tufty, who taught children about road safety in the 1970s. His chum, Willy Weasel, regularly got knocked down by passing cars but clever Tufty always remembered to look both ways.

Now comes Savvy Squirrel, who, with backing from the chancellor and a multi-year lump of advertising spend from the financial services industry, will try “to drive a step-change in how investing is understood, discussed and adopted”, as the blurb puts it. In translation: don’t squirrel everything away in a boring cash Isa but try taking an investment risk or two if you value your long-term financial health.

As with preventing road traffic accidents, the cause is noble. Every study on long-term financial returns reaches the same conclusion: inflation is the investor’s enemy and there is a cost to holding cash for long periods.

One statistical bible is the Equity Gilt Study published by Barclays, and a few numbers demonstrate the point. From 2004 to 2024, cash generated a return of minus 40.5% in real terms (meaning after inflation and including interest paid). By contrast, a conventional diversified portfolio comprising 60% UK equities and 40% gilts increased by 21.6% in real terms. A missed opportunity of 62.1 percentage points is enormous

Tufty the Squirrel and friends, part of a 1970s public information road safety series, is one of the UK’s favourite public information films. Photograph: National Archive/PA

Rachel Reeves’s interest in promoting the virtues of investment lies not only in helping savers but in greasing the wheels of the capital markets. Fair enough: a healthy economy needs a healthy stock market, including one that makes it easy for retail investors to participate. It is slightly ridiculous that the colossal sum of £610bn is estimated to be sitting in cash savings in the UK; it can’t all be rainy-day money or cash parked awaiting a house purchase.

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Many Americans famously follow the stock markets closely and discuss their 401(k) pensions savings plans but, even by European standards, the UK’s retail investment culture lags. Sweden has popularised investment with tax-breaks and other changes. Even supposedly cautious Germans are less inhibited. So, yes, one can applaud the ambition behind the campaign.

But here’s the doubt: it all feels terribly tame.

One can imagine an alternative launch in which Reeves tried to create a buzz by cutting stamp duty on share purchases. There are good reasons to adopt that policy anyway, as argued here many times, but a cut now would grab attention. True, rules for banks and investment firms on giving “targeted guidance” are being loosened to allow more useful advice alongside the “capital at risk” warnings. Yet the current news flow in Isa-land is about HMRC’s pernickety interpretation of the tax treatment of cash held within stocks and shares account. That just creates bad vibes in the wings.

Meanwhile, the campaign’s goals read as wishy-washy. It’s all about “helping people build confidence over time”, apparently. Well, OK, that’s what the market research suggests, but “creating more opportunities for everyday conversations” is limp when, in the outside world, teenagers are trading crypto on their phones and the world is awash with smart apps. The intended audience can surely handle more directness.

As for the squirrel, it may get lost in the forest of meerkats and other CGI creatures deployed by financial services firms. For a campaign that is supposed to be doing something distinctly different, why go with a character which, on first glance, looks generic?

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Back in the pre-smartphone 1970s, there was a certain shock value for the average five-year-old in seeing Willie Weasel lying injured in the road. At least the message about bad consequences was clear and memorable. One wishes the Savvy campaign well, but one fears a conversational squirrel may struggle to be heard.

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German finance minister wants to scrap spousal tax splitting

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German finance minister wants to scrap spousal tax splitting

Last weekend, several thousand people took to the streets in Munich to demonstrate against abortion and assisted suicide. One speaker made an extremely dramatic plea against what he called the “culture of death” that has allegedly taken hold in Germany. One sign of this, the speaker argued, was that the government is planning to abolish a regulation known as “spousal tax splitting.”

Is tax law really relevant to deep philosophical debates on the sanctity of life? It is even a matter of life and death at all? Surely we needn’t go that far? In any case, the intense political uproar surrounding the new debate on whether to abolish spousal tax splitting is notable, even by today’s standards of populist outrage.

An advantage for couples with widely divergent incomes

The row was sparked by Germany’s vice chancellor and finance minister, Lars Klingbeil, of the center-left Social Democratic Party (SPD), who said he wanted to abolish and replace the joint taxation of spouses’ income, a system that has been in place since 1958.

How exactly does spousal tax splitting work? In Germany, married couples (and since 2013, couples in civil partnerships), can choose to have their income assessed jointly by the tax authorities.

It means that the taxable income for both spouses together is halved – as if both partners had each earned an equal half of the income. Their tax liability is then determined by simply doubling the income tax due on one half.

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As people who earn more pay higher taxes in Germany, this system benefits couples where one partner (and often this is still the man) earns significantly more than the other (in practice often the woman).

Lars Klingbeil
Lars Klingbeil thinks spousal splitting is outdated and costs the state too muchImage: Bernd von Jutrczenka/dpa/picture alliance

Costs of up to €25 billion per year

If for example one partner earns €60,000 ($70,512) a year and the other partner earns nothing, the couple will be taxed as if they earned €30,000 each. In this example, the couple would save nearly €5,800 in taxes per year compared to the amount they would owe if both partners filed their taxes separately. According to the Finance Ministry, spousal tax splitting costs the government a total of up to €25 billion annually.

Some critics have long viewed splitting as a tool to keep women out of the labor market, because the more a woman earns, the larger her tax burden becomes. Klingbeil seems to agree, arguing on ARD television in late March that the system was “out of step with the times.” The spousal splitting system reflects “a view of women and families that is completely at odds with my own,” he said.

Chancellor Merz said to be in favor of splitting

On Monday of this week, Klingbeil got some surprising support on this from Johannes Winkel, head of the youth wing of the conservative Christian Democratic Union (CDU).

“Given the demographic reality, the government should create incentives to ensure that both partners in a relationship are employed,” Winkel told the Funke Media Group. “In the future, tax relief should primarily be granted to married couples when they are facing hardships related to raising children.”

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But the chancellor is a vocal skeptic of the proposal. “I am not convinced by the claim that joint filing for married couples discourages women from working,” Friedrich Merz said at a conference organized by the Frankfurter Allgemeine Zeitung newspaper. “Marriage is a relationship based on shared income and mutual support. And in a marriage, income must be treated as a joint income for tax purposes, not separately.”

Berlin under pressure to fix pensions, health care and taxes

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Klingbeil’s alternative plan

At around 74%, the labor force participation rate for women in Germany is one of the highest in Europe, but half of them work part-time.

Klingbeil’s idea is to replace the existing system with a more flexible approach: Both partners would be able to distribute tax-free income among themselves in such a way that it minimizes their tax liability. This would allow the couple to continue enjoying a tax advantage, albeit not to the same extent as before. And whether one partner earns more than the other would become less important.

However, it remains to be seen whether Klingbeil will be able to push through his proposal. Aside from Germany, similar regulations offering tax benefits to couples exist in Poland, Luxembourg, Portugal and France.

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This article was originally written in German.

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