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Wall Street’s best frenemy

Ken Griffin
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Wall Street underestimates Ken Griffin at its peril

News that Ken Griffin’s trading behemoth Citadel Securities — along with asset management giant BlackRock — are part of a group backing a new national stock exchange based in Dallas was largely shrugged off on Wednesday.

After all, other recent efforts to uproot lower Manhattan from its century-long position as the key chokepoint of global capitalism haven’t moved the needle much. Remember IEX? The Long-Term Stock Exchange? Both failed to make much of a dent in the dominant position of the New York Stock Exchange, Nasdaq, and CBOE.

And the $120 million in funding the new exchange, TXSE, was touting is — let’s face it — peanuts when it comes to the expense of building and maintaining the type of trading technology that would be needed to establish a reliable electronic exchange.

But this is missing something important: It’s called Ken Griffin.

The billionaire financier — a hedge-fund manager and market-making and trading technology entrepreneur — poses a unique competitive problem that Wall Street has repeatedly failed to solve in recent years, as his ever-expanding trading empire has been able to lop off larger chunks of business Wall Street once owned. (This is a big part of the reason Griffin is personally now worth more than $40 billion.)

(Disclosure: Sherwood News is an editorially independent subsidiary of Robinhood Markets, Inc. Citadel Securities has a business relationship with Robinhood.)

Making a market

Since Griffin established his market-making unit, Citadel Securities, in 2002, it has grown into a significant — and in some instances, dominant — player in businesses long controlled by Wall Street institutions.

Most of these businesses involve Wall Street’s core competency: matching buyers and sellers for a range of investments, including options, foreign exchange, and corporate and government bonds. Citadel Securities has also kicked in the door of the incredibly profitable interest rate swaps trading business that was long a cherished, and closely guarded, profit center for major Wall Street banks like J.P. Morgan, Goldman Sachs and Bank of America.

How has Griffin and his hand-picked executives been able to do it? Well, over the years, I’ve spoken privately with Wall Street traders and executives who say it has to do with the unique positioning Griffin’s empire has as Wall Street’s best frenemy.

Here’s what they say: While his trading division — he is the founder and largest shareholder in Citadel Securities, though no longer runs it day-to-day — is perhaps Wall Street’s biggest competitor, he is also the CEO of a $60 billion-plus hedge fund known as Citadel Advisors — legally distinct from the Citadel Securities trading arm — which is one of Wall Street’s biggest clients.

Essentially, Wall Street is terminally conflicted about how to respond to Griffin’s competitive incursions.

Executives are reluctant to declare an all-out competitive war with Griffin, for fear of A) losing and B) jeopardizing the lucrative trading commissions and prime brokerage business that his hedge fund throws their way. There’s also a C) wild card, in that in their heart of hearts, many of Wall Street’s elite executives could envision themselves occupying a well-compensated chair at Citadel some day.

Wall Street’s best frenemy

By the way, Citadel Securities could be said to have a similar frenemy position toward stock exchanges. While the company’s principal trading business — which uses its own capital to execute trades off exchanges — is a major competitor with exchanges, Citadel is also a major business partner of the NYSE and has been for a long time.  

Today, Citadel remains the NYSE’s top designated market maker. It has responsibility for managing trading in some 2,000 stocks, or about 65% of listings. That effectively makes Citadel Securities one of the one of the biggest business partners of the venerable stock exchange, which is owned by IntercontinentalExchange.

Political power

The Griffin-related risks don’t stop there for stock exchanges.

While the heavily regulated nature of public stock trading has long served as something of a competitive moat for exchanges, Griffin’s political muscle could help cut through the protective cocoon and red tape of exchanges.

Bottom line? Citadel Securities is already one of the most important nodes of the stock trading business, executing — that is, matching buyers and sellers — 23% of all publicly reported US trades last year.

It’s unclear how serious Citadel Securities is about putting financial or trading firepower behind any upstart stock exchange. (It has backed other exchanges in the past, perhaps most notably the Members Exchange or MEMX, in 2019.)

But by definition, any exchange, even an as-yet nonexistent one like the TXSE, seriously backed by Citadel Securities could be a threat. Wall Street, consider yourself warned.

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The slow burn in software stocks is erupting into an all-out bonfire

Good results? Doesn’t matter. Good guidance? Doesn’t matter. Spending a ton to augment your business with AI? You’d better believe it doesn’t matter.

This earnings season, investors have decided that AI is enough of a long-term threat to the earnings power of software companies that the past three months or the next 12 are, at best, the calm before the storm. And heaven help management teams that didn’t offer strong results or a positive outlook.

The slow burn in software stocks has erupted into an all-out bonfire on Thursday, fueled by traders finding any excuse to sell Microsoft and ServiceNow after both reported robust quarterly results. The follow-through is weighing on the likes of Atlassian, Workday, Salesforce, Datadog, and Intuit. Put it all together and iShares Expanded Tech Software ETF is poised for its worst day since the Friday following the Rose Garden reciprocal tariff announcements in April 2025.

Here’s how an assortment of software companies have done on the session after reporting earnings:

Are there babies being thrown out with the bathwater here? Maybe. Probably, even!

But it likely won’t inspire too much confidence to learn that the last time the S&P 500 Software & Services industry group was down at least 20% over a 63-session stretch while the SPDR S&P 500 ETF was positive happened to be June 12, 2000.

markets

Joby plunges after announcing plans to raise $1 billion in convertible bonds and stock

Shares of air taxi maker Joby Aviation are down more than 14% in premarket trading after the company announced a $1 billion capital raise after the bell Wednesday.

Joby, which in December said it would invest in equipment, facilities, and employees to double its aircraft production output by 2027, is offering convertible senior notes due 2032.

According to reporting by Bloomberg, the notes are being offered with an up to 30% conversion premium. Bloomberg reports that the company is pricing its share offering between $11.35 and $11.75, representing up to a 15% discount on the stock as of Wednesday’s close.

Joby ended its third quarter with $978.1 million in cash and cash equivalents, down slightly from its second quarter. Its shares have risen 62% over the past 12 months, compared to a more than 14% loss for its rival Archer Aviation in the same stretch.

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Why Meta is ripping higher after earnings while Microsoft craters

Two hyperscalers. Two top- and bottom-line beats. Two different reactions.

When both companies issue capex guidance that’s higher than expected and one goes up and the other goes down, it’s difficult for me to argue that the capex outlook is the key driver of either market reaction.

So here’s a smattering of potential reasons for the divergent paths of Meta and Microsoft since releasing quarterly earnings reports after the close on Wednesday, which has seen the former rally while the latter gets crushed:

  • Microsoft cloud growth is slowing; Meta’s top line is poised to accelerate.

    • Azure revenues were up 38% year on year in constant currency terms, a modest sequential slowdown since Q2 2025, and management’s guidance for growth of 37% to 38% in the current quarter implies this trend is likely to continue.

    • The midpoint of Meta’s guidance for revenues between $53.5 billion and $56.5 billion this quarter would mark an acceleration to sales growth of 30% year on year. Since the AI boom started, its high-water mark for sales growth has been 27%.

  • Customer quality and concentration matters:

    • While Microsoft enjoyed solid ex-OpenAI growth in its remaining performance obligations, that one customer is still responsible for 45% of commercial RPO. Look at Oracle to get a glimpse of what investors think about firms whose AI build-outs use OpenAI demand as scaffolding.

    • Meta’s lack of a cloud business has been an oft-cited negative about the aggressiveness of its build-out. The company arguably has to work harder than other hyperscalers to turn that spending into sales growth. And... that’s happening.

  • Initial conditions matter:

    • There was probably a little more embedded pessimism on Meta than Microsoft heading into these reports. As of Wednesday’s close, it was the only member of the Magnificent 7 to trade lower over the past 12 months.

Cheers to Duncan Weldon, VKMacro, and George Pearkes, whose back-and-forth on Bluesky inspired this post.

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Microsoft just delivered a big blow to Michael Burry’s AI bear case

Microsoft’s chief financial officer, Amy Hood, just offered some intel that severely undercuts Michael Burry’s argument against AI stocks, albeit with one big caveat.

If you’ll recall, the hedge fund manager turned Substacker of “The Big Short” fame said that tech companies were understating depreciation charges — that is, how fast GPUs lose their value over time, in a bid to artificially juice profits.

During Microsoft’s conference call on Wednesday, the CFO was asked how the company will be able to capture enough revenue over the six-year useful life of the hardware to justify the outlays. Her response:

“The way to think about that is the majority of the capital that were spending today and a lot of the GPUs that were buying are already contracted for most of their useful life,” she said. “And so a way to think about that is much of that risk that I think youre pointing to isnt there because theyre already sold for the entirety of their useful life.”

The implication here is that not only will these chips make money for as long as tech companies expect they will, but that their useful economic life might actually be longer than that, not shorter.

This tidbit is obviously positive for the hyperscalers, which are spending hundreds of billions on these GPUs. But it’s probably even more of a relief to neoclouds that are even more dependent on these chips being able to generate cash. That’s (mostly) all there is to their businesses, unlike megacap tech giants.

It also corroborates commentary from one such neocloud, CoreWeave, on how well these processors retain value.

“For example, in Q3, we saw our first 10,000-plus H100 contract approaching expiration,” CoreWeave CEO Michael Intrator said after the firm’s most recent earnings report. “Two quarters in advance, the customer proactively recontracted for the infrastructure at a price within 5% of the original agreement.”

And per Silicon Data, H100 rental rates have firmed significantly since the end of November.

However, I’d be remiss not to point out a potential fly in the ointment here: one reason that Microsoft’s GPUs are contracted for most of their useful life is thanks to demand from OpenAI, which accounts for 45% of its commercial remaining performance obligations.

And, if Oracle’s shown us anything, it’s that customer concentration and quality matters.

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Nvidia, Microsoft, and Amazon reportedly in talks to invest up to $60 billion in OpenAI

OpenAI is bringing in more revenue than ever, but with ambitions to spend north of $1 trillion on its AI infrastructure build-out — cash that it simply does not have to hand — it’s maybe no surprise that the company is almost constantly in fundraising mode.

And its latest discussions could see the company raise as much as $60 billion from three of its biggest suppliers, with The Information reporting that Nvidia, Microsoft, and Amazon may anchor a larger round that could see the ChatGPT maker raise as much as $100 billion.

Per The Information’s sources, existing investor Nvidia is in discussions to invest up to $30 billion, new investor Amazon is considering $10 billion to more than $20 billion, while Microsoft, which is also already heavily invested with a 27% stake, is looking at less than $10 billion.

Separately, reporting from the Financial Times confirms some of the same broader details, like that the three tech companies are indeed close to participating in a larger ~$100 billion round. However, the sources cited by the FT put the combined total investment from the trio of tech titans closer to $40 billion.

While OpenAI is close to receiving term sheets, or an investment commitment, from these companies, according to The Information, their investments could depend on other deals that they are already negotiating with OpenAI separately, including its cloud server rental deal with Amazon.

Earlier this week, reports emerged that SoftBank might plow a further $30 billion into OpenAI as well — presumably as part of this larger round.

And its latest discussions could see the company raise as much as $60 billion from three of its biggest suppliers, with The Information reporting that Nvidia, Microsoft, and Amazon may anchor a larger round that could see the ChatGPT maker raise as much as $100 billion.

Per The Information’s sources, existing investor Nvidia is in discussions to invest up to $30 billion, new investor Amazon is considering $10 billion to more than $20 billion, while Microsoft, which is also already heavily invested with a 27% stake, is looking at less than $10 billion.

Separately, reporting from the Financial Times confirms some of the same broader details, like that the three tech companies are indeed close to participating in a larger ~$100 billion round. However, the sources cited by the FT put the combined total investment from the trio of tech titans closer to $40 billion.

While OpenAI is close to receiving term sheets, or an investment commitment, from these companies, according to The Information, their investments could depend on other deals that they are already negotiating with OpenAI separately, including its cloud server rental deal with Amazon.

Earlier this week, reports emerged that SoftBank might plow a further $30 billion into OpenAI as well — presumably as part of this larger round.

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