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🍋 Closing Deals in the DMs

🍋 Closing Deals in the DMs

Plus: OpenAI could file for IPO as soon as tomorrow, tech buyouts have nearly ground to a halt, and Bezos says bottom half of earners should pay zero in income taxes.

Short Squeez
May 21, 2026

Together With

“We shouldn’t be asking this nurse in Queens to send money to Washington. They should be sending her an apology. It really makes no sense.” — Jeff Bezos

Good morning! OpenAI is preparing to file for an IPO as soon as tomorrow, working with Goldman Sachs and Morgan Stanley. Nvidia beat on revenue and added $80 billion to its buyback (plus a 25x dividend hike).

Jeff Bezos says the bottom half of earners should pay zero in income taxes. Goldman says the US labor market is healthier than when ChatGPT launched. Tech private equity is effectively frozen, with just $9.3 billion in global tech buyout value across April and May combined.

Plus: Lazard's CEO says the US economy is now a levered bet on AI. And how Google is starting to win the AI race.

Discover a simpler way to evaluate your retirement income options.

SQUEEZ OF THE DAY

Closing Deals in the DMs

Investment banking used to work one way. Build the relationship over a decade, fly out to the client, walk in with the pitchbook, pretend league-table positioning isn't everything, and hope you get lead-left. Now you also slide into Elon's DMs.

Goldman CEO David Solomon personally messaged Musk while Goldman fought Morgan Stanley for the top spot on SpaceX's IPO, which is targeting a valuation north of $2 trillion and up to $75 billion in proceeds. If it prices anywhere near that, it blows past Saudi Aramco's $29.4 billion record and becomes the largest IPO in history.

Morgan Stanley has been Musk's house bank for years, stuck with him through the Twitter deal, ate real balance-sheet pain when the debt got stuck, and Jared Birchall, Musk's right-hand man, is a former MS employee. They even brought back Michael Grimes as chairman of investment banking in February, partly to lead this exact deal.

Goldman pitched it like a Super Bowl mandate. Solomon DM'd Musk. The deal team got stacked with Dan Dees, Kim Posnett, David Ludwig, and Susie Scher. They pitched the entire Musk empire, not just SpaceX. And when the filing dropped, Goldman was listed ahead of Morgan Stanley. Morgan Stanley says it's alphabetical and they're co-leads. Sure.

SpaceX did $18.6 billion in revenue in 2025, up 33% YoY, but swung from a $791 million profit in 2024 to a $4.94 billion loss. Starlink is the printer, subscribers doubled to 10.3 million and connectivity income hit $4.42 billion. xAI, now folded in, lost $6.4 billion.

Notably, Anthropic is paying SpaceX $1.25 billion a month through May 2029 for compute, roughly $15 billion a year of baked-in revenue. Musk keeps 85.1% of voting power, so anyone buying in is along for the ride, not the steering. Marketing kicks off June 4, pricing around June 11, with 23 banks on the deal.

Takeaway: When a company tries to raise $75 billion, every bank on the Street suddenly discovers "deep conviction in the space economy." But it also shows how investment banking is changing in the internet economy. Sure, relationships still matter, but online touchpoints are a whole other layer now, and Solomon was on it. If the CEO of Goldman Sachs can get a deal done by sliding into the DMs, surely you can at least get a gf.

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HEADLINES

Markets Rundown

Market Update

U.S. equities rallied sharply as optimism grew around a potential U.S.-Iran peace agreement
President Trump said negotiations with Iran are in the “final stages,” helping push WTI crude oil nearly $10 lower to around $98 per barrel
The Russell 2000 surged 2.4%, while the S&P 500 and Nasdaq each gained between 1% and 1.5%
Treasury yields declined as lower oil prices eased inflation concerns, with the 10-year Treasury yield falling 10 basis points
The U.S. dollar weakened, while gold prices climbed back above $4,500 per ounce

Fed Signals Higher-for-Longer Rates

Fed minutes highlighted growing disagreement among policymakers around future rate direction
Several officials favored removing the Fed’s prior easing bias, signaling rates could potentially move either higher or lower
Markets have largely priced out near-term rate cuts and are increasingly considering the possibility of future hikes if inflation remains elevated
The broader expectation remains that the Fed will likely hold rates steady while monitoring energy-driven inflation pressures

Movers & Shakers

(+) Toll Brothers ($TOL) +10% after the homebuilding company raised its full-year guidance.
(+) United Airlines ($UAL) +10% because of strong ticket demand and a dip in oil prices.
(–) Reddit ($RDDT) -5% after the company’s CEO sold $2.8M of shares last week.

Prediction Markets

The implications with this earnings call: discretionary spending, grocery inflation, and e-commerce trends.
Trade on real-world events with Kalshi. Use code OWS to get a $10 bonus when you trade $10.

Private Dealmaking

Radar, a retail intelligence platform, raised $170 million
Vi, a maker of healthcare AI agents, raised $145 million
SendCutSend, an on-demand manufacturer, raised $110 million
Fragile, a startup powering consumer hardware subscription programs, raised nearly $100 million
Commure, a healthcare workflow platform, raised $70 million
Accro Bioscience, a Chinese biotech focused on immune-mediated diseases, raised $50 million

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

BOOK OF THE DAY

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DAILY VISUAL

America's Data Center Count Is About to Nearly Double

Source: Apollo

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DAILY ACUMEN

Asymmetry of Time

A day spent doing the right work compounds over decades. A day spent doing the wrong work compounds in exactly the same way, just in a direction you did not intend.

The two days feel identical in the moment. They look identical on a calendar. The difference only becomes visible at a distance, when you suddenly realize that ten years of one trajectory has built something extraordinary and ten years of the other has built almost nothing at all.

The frustrating part is that you cannot tell, in real time, which kind of day you are having. The signal is too weak. The work feels like work. The progress feels like progress. Whether it adds up to something matters enormously, and that question only gets answered slowly, in retrospect, by a future version of you who will inherit the consequences of how you spent right now.

Time is not a resource you manage. It is a verdict you receive, eventually, on how seriously you took the question of where it should have gone.

ENLIGHTENMENT

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The mathematical reason most people never make it
5 ways to unlock the best in yourself
Startup says it can read your brain using a pair of headphones
Why the Farmer’s Carry is the ultimate strength test
2 reasons why intelligent people face higher loneliness

MEME-A-PALOOZA

Memes of the Day

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