Short Squeez
Posts
🍋 AI Trainers Are Printing Money

🍋 AI Trainers Are Printing Money

Plus: Anthropic picks GS and Morgan Stanley to lead IPO, DeepSeek raising at $52B valuation, Broadcom plunges after earnings and PE stocks sold off on withdrawal cap fears.

Short Squeez
June 04, 2026

Together With

“Without self-belief nothing can be accomplished. With it, nothing is impossible.” — Felix Dennis

Good Morning! Anthropic has picked Morgan Stanley and Goldman Sachs to lead its IPO. SpaceX plans to market its offering at $135 per share at a $1.77 trillion valuation, which would make it the seventh-largest company in the US, surpassing Tesla's $1.6 trillion market cap.

Bank of America hired 2,000 summer interns and another 2,000 full-time entry-level analysts, bucking AI job fears. DeepSeek is raising $7.4 billion at a $52 billion valuation, a reminder that America's AI trinity faces viable competition from China. And KKR, Ares, and Blackstone all tumbled after Partners Group capped private equity fund withdrawals.

Plus: How remote work may be fueling youth unemployment, and why white-collar workers can't get ahead.

There’s a new product for private markets deal teams that hosts all deal materials and syncs to historical firm knowledge. Learn more about Spaces today.

SQUEEZ OF THE DAY

AI Trainers Are Printing Money

Wall Street is spending billions on AI. The problem is a lot of bankers still don’t know how to use it beyond “summarize this PDF.”

That gap has created a very lucrative new gig: AI trainers for finance. Felipe Sinisterra and Dave Wang, two former SoftBank investors, now charge up to $25,000 a day teaching bankers, investors, and fund managers how to actually wire AI into their workflows. Their firm, Wall Street Prompt, has reportedly worked with T. Rowe Price, Citi, and Bank of America, and they're already booked out two months.

In one session, Wang showed a venture fund how Gemini could analyze founder pitch videos, cross-referencing transcripts against body language and facial cues to flag red flags. Sinisterra then showed how ChatGPT and Claude could scan earnings-call transcripts, surface market-moving statements, run sentiment analysis, and turn management commentary into forecast inputs. Translation: the machine is coming for the most annoying parts of the analyst job first.

That's why banks are paying attention. JPMorgan rolled out its LLM Suite to most employees. Goldman is building AI agents with Anthropic. Bank of America says its 18,000 developers are 20-25% more productive. Meanwhile, Standard Chartered is prepping to cut thousands of support roles, and Citi, Wells Fargo, and BofA cut more than 5,000 jobs in Q1 2026 despite a record earnings season. So yes, it's about efficiency. It's also about fewer humans doing repetitive work.

The uncomfortable part is the skill gap inside the banks. Some employees are becoming power users. Others still treat ChatGPT like a suspicious intern with WiFi. One recruiter put the range as "Luddite to AI super-adopter." Being good at Excel, PowerPoint, accounting, or valuation may no longer be enough. The next filter is whether you can use AI to do that same work faster, cleaner, and at scale.

The junior-bankers-should-pay-attention angle is obvious. AI probably does not eliminate judgment, relationships, or senior-level decision-making anytime soon. But it absolutely attacks the bottom of the pyramid: first-pass research, transcript summaries, diligence notes, comps, pitchbook drafts, and “can you pull every mention of pricing pressure from the last eight earnings calls?” One consultant in the piece said skilled people with AI tools could do 10-20x more, with far fewer analysts and associates needed.

Takeaway: Wall Street's AI problem is no longer access to the tools, it's knowing what to do with them. That's why two ex-bankers can charge $25K a day to teach people how to automate the grunt work that used to define the job. Firms that crack it get faster analysts, leaner teams, better margins. Workers who crack it get more valuable. Everyone else risks becoming the human assembly line Goldman already wants to replace. Knowing your hotkeys used to make you a good analyst. Knowing AI might be the new version.

PRESENTED BY BLUEFLAME AI

10 Tabs, Now 1 Space

Private market work runs on detail, and those details rarely sit in one place. CIMs, transcripts, broker reports, and email threads are scattered across VDRs, CRMs, and shared drives. As the team goes through them, a shared view gets hard to maintain, onboarding new teammates drags, and every conversation tends to restart from scratch.

Blueflame's Spaces gives you a single home for anything you need, from connected files to notes and agent chats. These live together in the Space under existing firm permissions, so the full context stays in one place and persists from one session to the next.

A few ways teams put them to work:

Deal diligence from one shared information set
Market and competitor research, tracked over time
LP fundraising notes, touchpoints, and follow-ups
Q&A drafting against a live data room

Find out if Blueflame is right for your firm. Book a demo today.

HEADLINES

Markets Rundown

Market Update

U.S. equities moved lower following a strong run
Higher oil prices and rising Treasury yields weighed on sentiment and pushed markets into a risk-off tone
Energy and consumer staples outperformed, while technology and financials lagged
Small-cap stocks underperformed as investors weighed geopolitical uncertainty and higher energy costs

Inflation Continues to Complicate the Fed Outlook

Inflation pressures remain elevated, with the Fed’s preferred inflation gauge running above target and showing limited signs of rapid improvement
Headline inflation has been supported by higher energy prices, but underlying inflation measures also remain stubbornly high
Markets continue to price in the possibility of tighter policy over the next year, though the hurdle for additional hikes remains elevated
Strong growth and sticky inflation create a difficult balancing act for policymakers

Movers & Shakers

(+) GameStop ($GME) +6% after reporting record Q1 net income of $389.6M on revenue of $835.3M driven by its growing collectibles business.
(–) Palo Alto Networks ($PANW) -6% because the solid Q3 beat was met with sell-the-news profit-taking.
(–) Intuitive Machines ($LUNR) -5% after announcing a $500M at-the-market stock offering through ten agents including Barclays and Cantor Fitzgerald.

Prediction Markets

Surely some of y’all are working on these deals…
Trade on real-world events with Kalshi. Use code OWS to get a $10 bonus when you trade $10.

Private Dealmaking

NewLimit, a longevity pharma startup, raised $435 million
AlphaSense, a market research platform, raised $350 million
Oxford Quantum Circuits, a quantum computing startup, raised around $350 million
Cyera, a data security company, raised $300 million
Coralogix, an observability startup, raised $200 million
Factorial, a provider of workforce management software, raised $150 million

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

BOOK OF THE DAY

Make Money Easy

Description:
A practical and mindset-focused guide from Lewis Howes on rethinking wealth, financial freedom, and the relationship people have with money. The book blends personal finance principles with psychology and habit formation, arguing that building wealth is as much about mindset and behavior as it is about tactics. It focuses on removing limiting beliefs around money, creating sustainable financial systems, and designing a life that feels rich beyond just dollars.

Book Length: 272 pages
Release Date: May 27, 2025

Ideal For:
Anyone looking to improve their relationship with money, build financial freedom, and create a more intentional approach to wealth and life design.

Making money easier starts when you stop treating wealth as only a financial problem and start treating it as a behavioral one.

DAILY VISUAL

AI Boosting Business Formation

Source: Apollo

PRESENTED BY MOSAIC

Mosaic Introduces Major Upgrades to FactSet Integration and Take-Private Analysis

Mosaic continues to enhance its FactSet integration and take-private analysis capabilities, enabling users to automatically pull live share prices, broker targets, market data, and VWAP metrics directly into AVP outputs.

Teams can now incorporate premium-to-L3M and premium-to-L6M VWAP analyses with greater accuracy, while flexible line-item controls allow each VWAP metric to be toggled on or off to customize outputs.

These updates streamline valuation workflows, improve data accessibility, and provide deal teams with deeper insights and greater efficiency across the Mosaic platform.

Demo the platform today.

DAILY ACUMEN

Pre-Mortem

Most people do a post-mortem after a decision fails. The far more valuable exercise is to do it before. Imagine yourself two years out, looking back at a decision that went badly wrong, and ask in detail how it happened. The specificity of working backward from an assumed failure surfaces risks that forward-looking optimism reliably hides.

The psychology is the key. When you ask what could go wrong, the brain politely lists a few obvious concerns and moves on. When you assume it already went wrong and ask why, the brain treats it as a memory to be explained rather than a hypothetical to be dismissed, and the honesty of the answers changes completely. Suddenly the assumptions you were quietly relying on become visible.

The best risk management does not happen when things are falling apart. It happens in the quiet moment before you commit, when you are still willing to imagine that you might be wrong.

ENLIGHTENMENT

Short Squeez Picks

Why employees hurt their career by staying in jobs they’ve outgrown
The more you care about work, the more it can burn you out
How the rules of getting rich in America change every era
11 back exercises that will improve your posture
The most underappreciated communication skill that can save a conversation

MEME-A-PALOOZA

Memes of the Day

📣 Partner With Us: Get in front of an audience of over 1 million finance professionals, business leaders, and policy influencers. Submit a partnership inquiry.

📊 Wall Street Comp & Culture Data: Get the most detailed comp, carry, and culture insights across 800+ Wall Street firms. Explore the data.

📈 Grow With Us: Work directly with the Overheard on Wall Street team to scale your finance brand. Schedule your free consult.

🧢 Wall Street Shop: Explore our collection of finance-themed apparel and merchandise. Visit the shop.

📬 Deals Newsletter – Buysiders: A curated roundup of major M&A, private equity, and VC activity. Plus access to private deal flow. Subscribe here.

What'd you think of today's edition?

Reply

or to participate.