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“The more complicated the system, the easier it is to fool yourself.” — Morgan Housel

Good Morning! A Miami developer made a $1B gain selling land to Ken Griffin for Carnegie Mellon's new Miami campus. Goldman's top 20 executives are set to unlock a special bonus worth $500M+ combined, with David Solomon taking home over $100M.

Starbucks is eyeing Chipotle in what could be the largest acquisition in restaurant history, and Vance says the US will suspend Microsoft from the green card program. Jeff Bezos says AI could enable three-day workweeks, and Tottenham's Xavi Simons enrolled at Harvard Business School while recovering from a torn ACL.

Plus: a Lincoln Park billionaire was accused of fueling a rat infestation in Chicago, and how to make friends in a new city.

Make that hefty NYC monthly rent start working for you. Earn points for it with the Bilt Card. Learn more about it here.

SQUEEZ OF THE DAY

OpenAI’s $20B Footnote

OpenAI has been planning one of the largest IPOs in history, which the company’s management recently pushed back to at least 2027 over AI safety concerns. But in addition to needing time to build some guardrails around new models, the company apparently might need time to find another $20 billion in revenue it had been mistakenly reporting.

Yesterday, new financial documents showed that OpenAI is approaching around $50 billion of annualized revenue through September, which sounds healthy but is about $20 billion below the $70 billion figure that had been widely reported just days earlier. 

And, even though OpenAI isn’t public, it’s still one of the most important companies in the world, and Wall Street noticed. AI-linked stocks sold off after the report, and Nvidia closed down 3%. Oracle closed down more than 5%. Some investors were already nervous about all the debt needed to finance the AI buildout, and finding out that OpenAI’s headline revenue run rate was materially lower gave them another reason to revisit the model.

The good news is that OpenAI didn’t exactly lose $20 billion. Part of the discrepancy comes down to how investors were trying to compare OpenAI with Anthropic. Anthropic includes revenue generated through cloud partners like AWS and Google Cloud in some of the run-rate figures investors use, and OpenAI doesn’t. So investors were effectively grossing up OpenAI’s number to make the two companies more comparable. But still, markets don’t love discovering that one of the most important numbers in AI needs a reconciliation.

And OpenAI is still losing money while committing enormous sums to chips, data centers, and computing capacity, and the entire AI trade increasingly rests on the assumption that revenue will grow quickly enough to justify hundreds of billions of dollars of infrastructure spending underneath it. So whether the industry’s flagship private company is running at $50 billion or $70 billion is not exactly an accounting detail.

Takeaway: $50 billion is still an absurd number. OpenAI generated a little over $20 billion of annualized revenue at the end of 2025, and the company is still growing at an absolutely insane pace. The problem is that when investors are discussing a $1.4 trillion valuation, “the business is growing insanely fast” and “the business is growing as fast as everyone thought” become two very different questions. 

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HEADLINES

Top Reads

  • Ken Griffin's Miami deal gives Wynwood real estate developer Mana $1B win (BB)

  • Goldman's top leaders set to score more than $500 million with special bonus (BB)

  • OpenAI annualized revenues $20 billion less than previously signaled: report (CNBC)

  • Microsoft is being suspended from program to apply for green cards for H-1B visa workers, Vance says (WSJ)

  • AI could allow for 3-day workweeks and single-income households, Bezos claims (Forbes)

  • Tottenham’s Xavi Simons enrolls at Harvard Business School (talkSPORT)

  • Lincoln Park billionaire accused of fueling rat infestation (Axios)

  • AI startup Manus raises $500 million in first funding round since Meta breakup (CNBC)

  • Inflation on many everyday items was entirely due to tariffs, NY Fed says (CNBC)

  • Tiger Global poised for $5 billion windfall on early OpenAI bet (BB)

  • Chipotle jumps after report that Starbucks has explored takeover (BB)

  • How Ken Griffin's $3 billion could reshape higher education (BB)

  • Josh Kushner builds $17.5 billion empire beyond venture capital (BB)

  • How 7.4% mortgages are giving buyers leverage in a stuck housing market (WSJ)

CAPITAL PULSE

Markets Rundown


Market Update

  • Stocks closed lower as tech underperformed after OpenAI reported annualized revenue that missed expectations.

  • WTI crude traded near $91 as energy companies shut infrastructure ahead of Hurricane Isaias.

  • The 10-year Treasury yield eased to near 5.23% on solid auction demand, and the U.S. dollar weakened.

Economic Data

  • Initial jobless claims fell to 197,000, below the 200,000 forecast.

  • Continuing claims rose modestly to 1.72 million, slightly above the 1.70 million forecast.

  • Limited layoffs give the Fed room to stay focused on inflation as energy prices remain elevated.

Fed Outlook

  • Fed minutes showed most policymakers see another hike as likely appropriate by year-end, with 16 of 18 officials projecting at least one more this year.

  • For 2027, eight officials project one more increase while 10 expect no change or a cut.

  • Two more quarter-point hikes are expected over the next year, bringing the fed funds rate to about 4.5%.

Movers & Shakers

  • (+) Chipotle ($CMG) +6% after reports that Starbucks has explored a takeover of the burrito chain.

  • (–) Oracle ($ORCL) -6% because OpenAI's annualized revenue is reportedly about $20 billion below the figure previously circulated.

  • (–) CoreWeave ($CRWV) -8% after the AI cloud infrastructure company was dragged lower in the same selloff in AI stocks.

Prediction Markets

  • The Nobel Prize for Economics will be announced on Monday.

  • Trade on real-world events with Kalshi. Use code OWS to get a $10 bonus when you trade $10.

Private Dealmaking

  • Manus, a Chinese AI agent startup, raised over $500 million

  • Oratomic, a quantum computing startup, raised $475 million

  • Type One Energy, a fusion startup, raised $200 million

  • Matchpoint Therapeutics, a precision medicine biotech, raised $150 million

  • Veir, a developer of superconducting power delivery systems, raised $110 million

  • Parallel, an autonomous electric freight rail startup, raised $100 million

For more PE, VC & M&A deals, subscribe to our Buysiders newsletter.

BOOK OF THE DAY

When Everyone Knows That Everyone Knows

Description:
Steven Pinker explores one of the most fascinating and underappreciated forces shaping human behavior: common knowledge, or the things we know that other people know, and that we know they know, and so on. Pinker shows how this seemingly abstract idea helps explain financial bubbles and crashes, political movements, social conventions, diplomacy, relationships, and even awkward everyday interactions. He combines psychology, economics, game theory, linguistics, and evolutionary science to explain why people sometimes openly acknowledge what everyone already knows, while at other times they go to extraordinary lengths to pretend that nobody knows. The result is a fascinating framework for understanding how shared awareness coordinates societies, creates collective action, and can suddenly cause entire groups of people to change their behavior.

Book Length: 364 pages
Release Date: September 23, 2025

Ideal For:
Investors, economists, entrepreneurs, psychologists, political thinkers, and anyone interested in behavioral finance, game theory, social dynamics, human psychology, and understanding why markets and societies sometimes move collectively.

“Knowing something is powerful. Knowing that everyone else knows it can change everything.”

DAILY VISUAL

AI This, AI That

Source: Apollo

PRESENTED BY MOSAIC

Reverse LBOs are Here

Higher financing costs and tighter return thresholds have made entry price more consequential than ever. Buyers have less room for error, while bankers increasingly need to understand how far sponsors can stretch on valuation in a live process.

Mosaic’s new Reverse LBO helps answer that question quickly.

Enter a target IRR or MOIC, and Mosaic works backward to calculate the maximum purchase price, entry multiple, or bid premium that supports the required return. As growth, margins, leverage, financing costs, or other assumptions change, the answer updates automatically.

For bankers, that means a faster way to frame sponsor bid capacity, pressure-test valuation, and run scenarios during a process. For PE teams, it means quickly understanding how much they can pay while still preserving target returns.

See a Reverse LBO in action.

DAILY ACUMEN

Simpson’s Paradox

In 1973, UC Berkeley’s graduate programs admitted about 44 percent of male applicants and about 35 percent of female applicants. It looked like clear bias against women.

Then researchers split the data by department. In most departments, women were admitted at rates equal to or higher than men. Women had applied more often to the most competitive departments, where almost everyone gets rejected, and that dragged down their overall rate.

A trend can reverse once you split the data by a hidden variable. It happens in business constantly. A company’s blended margin can rise while every product’s margin falls, simply because the mix shifted toward the higher-margin product.

Before trusting any headline average, ask what is hiding inside it, and split the data by segment, cohort, or channel.

ENLIGHTENMENT

Short Squeez Picks

  • Stop developing your leadership

  • Kind Snacks founder on the advice on failure he gives kids 

  • Successful people share 1 habit to ask for help

  • How owning vs renting impacts your productivity

  • How to make friends in a new city

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