The Wall Street Skinny

Hosted by Kristen and Jen

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Episodes

258

Latest episode

Aug 2026

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EN-US

About the show

If Bloomberg and Bravo had a baby. Join us -- Kristen and Jen -- two former Morgan Stanley and Lehman Brothers investment bankers who take the most complex deals, market moves, and stories in finance and distill them into what actually matters.  From conversations with the biggest names in investing to deep dives people can’t stop sharing (not to mention the occasional HBO Industry red carpet), this is the show Wall Street is obsessed with.

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60 recent

August 19, 202636 min

Is a Private Credit scandal brewing behind the LA Lakers Sale?

The LA Lakers --- a prestigious basketball franchise that didn't change hands for 46 years --- just sold twice in ten months, the second time for $2.5 billion more than the first. The seller is Mark Walter, CEO of Guggenheim, owner of the Dodgers and part of Chelsea FC, and the man whose laptop and phone the FBI seized off his private jet just as the Lakers deal was coming together. Since then, one of the insurance companies in his orbit has revised its reported related-party investments from $1.4 billion to $17 billion. Quite the rounding error. In this episode, we get into the questions everyone on the Street is suddenly asking. Why would anyone sell the crown jewel of American sports a year after fighting to buy it? What do a bunch of boring life insurance companies most people have never heard of have to do with the trophy assets of the billionaire class? Why do private equity and private credit firms keep buying insurers in the first place — and what happens to that entire model when the disclosures around "related parties" turn out to be, let's say, incomplete? And why did Josh Kushner and Bob Iger, who spent months chasing a Las Vegas expansion team, pivot to the Lakers over a single weekend? The bigger question hanging over all of it: this structure — asset managers selling their own loans to insurance companies they control — underpins a massive share of the boom in private credit. If regulators start pulling on this thread, how many other portfolios look like this one? By way of disclaimer, no charges have been filed and no wrongdoing has been established nor is implied here; our research merely summarizes reporting from Bloomberg, the FT, the WSJ, and the LA Times.

August 12, 202651 min

OpenAI's Lawyer: How Big Tech is Winning the AI Race in the Courts

We got to sit down with John Quinn — the "Quinn" of Quinn Emanuel — one of the most powerful litigators in the world, and the man whose firm is defending OpenAI right now. What does someone at the very top of the legal food chain see coming that the rest of us don't? And why does he think one of the oldest concepts in law is about to become the most valuable weapon in tech? Here's what pulled us down this rabbit hole. The most valuable companies on earth are pouring hundreds of billions into inventions almost none of them can legally protect. So how do you build a moat around something you're not allowed to own? Why are Apple and OpenAI trying to destroy each other in one courtroom and sitting on the same side in another? And what does any of this have to do with a viral park bench kiss that blew up one of the big law talent poaching deals? We get into all of it: why the patent wars fell by the wayside, what actually replaced them, and why every giant pay package in tech, finance, and now law is really a fight over the one thing no company can lock in a vault. Then John tells us where he thinks this is all headed — for the AI giants, for the lawyers, and for anyone thinking about the profession at all.

August 5, 202629 min

SpaceX: Revisiting the IPO and What Comes Next

After the largest IPO in history, only about 5% of SpaceX — roughly $83 billion of the $1.75 trillion — is actually free to trade. Insiders are locked up, the banks that underwrote the deal can't lend shares to short sellers, and index funds are being forced to buy as SpaceX joins the Nasdaq-100 and the Russel. In this episode, Jen and Kristen, both former Morgan Stanley investment bankers, break down how the IPO was engineered — and the question every SpaceX investor should be asking: what happens when all that locked-up stock can finally sell? First, we cover what is normal in an IPO so you can see what isn't. We cover price talk vs. the $135 take-it-or-leave-it pricing, the green shoe, perpetual futures, and the fast-track Nasdaq-100 inclusion pulling in billions of passive buying. We lay out the risks, meaning the the wall of supply coming. Unlike the standard 180-day lockup, SpaceX is staggering its release: the first ~$240-500+ billion of stock unlocks after the first earnings report around September, with more tranches every few weeks after that — over $1 trillion freely tradeable by December, on the way to a ~$2 trillion overhang once Elon Musk's one-year lockup rolls off. But we also lay out why the passive buying actually helps dampen that supply PLUS why many institutional investors are NOT bearish on the stock despite the insane valuation.

July 31, 202629 min

The Biggest Hedge Fund Blow-Up of 2026 EXPLAINED: Situational Awareness

What took Situational Awareness from a $45bn hedge fund down to a $10bn hedge fund in less than a month? Two years ago Leopold Aschenbrenner was a researcher at OpenAI who wrote a 165-page essay about superintelligence. Since then, he raised $225 million seed funding from Stripe co-founders, Jane Street, and GitHub's CEO, which he proceeded to turn into an AI hedge fund called Situational Awareness worth about $45bn as of the beginning of July. He did this with no prior trading experience, 4-5x leverage on a concentrated bet in AI names. By Thursday the fund was down to about $10 billion. Neither Millennium nor Jane Street were willing to step in to catch a falling knife. Ultimately Citadel stepped in to buy the flagging portfolio. Here is the crazy part though: Aschenbrenner wasn't wrong. He is reportedly still up around 80% on the year and "he only sold enough to cover his losses". But what caused a massive drop in the global markets was that a prime broker does not care what happens in 2030. And because half the market was crowded into the exact same names, his exit was everyone else's problem. SK Hynix and CoreWeave cratered. Korea's Kospi tripped circuit breakers. Over a million retail accounts got margin called. All of July's violence, the moves that had traders questioning their own sanity, was one book being taken apart in public. So the question this episode actually asks is whether this was one overlevered fund or the first crack in the AI trade itself. Because the market's answer this week was a shrug. Microsoft just posted the largest single-day market cap gain in history and credit spreads snapped back tighter, as if the whole thing was somebody else's accident. Kristen and Jen have both traded through cycles that ended this way, and they have seen exactly how comforting that shrug feels right before it stops being true.

July 30, 20261 hr 0 min

What Just Happened to AI Stocks??

*Note: This episode was recorded before news broke of Situational Awareness' unwind, which gives us much better insight into the pace and magnitude of the move in the Korean markets specifically.* Chips, China, and credit. The three forces tearing through the AI trade right now, and we called it last week. In this episode we break down why the bond market cracked first, what widening credit spreads on Nvidia, Meta, and Oracle are actually telling you about default risk, and why the Nasdaq is bleeding while the S&P barely flinches. We walk through Alphabet's first negative free cash flow after twenty years of printing money, the CapEx numbers that keep getting revised upward, and the moment the market stopped rewarding spending and started punishing it. If you have ever wondered how to read a credit spread, we show you the math live. Then we get into the China story that moved markets this week. CXMT went public in the largest mainland Chinese semiconductor IPO on record, oversubscribed 212 times, and the Korean stock exchange took the hit because the KOSPI is essentially a memory-chip index wearing a trench coat. We explain why memory matters in an AI data center, why Samsung, SK Hynix, and Micron controlling 90 percent of the market was the whole moat, and what reports of domestically produced DUV lithography machines would mean for US export controls. We also unpack Nvidia guaranteeing borrowing for a 10-gigawatt OpenAI data center in Ohio, and whether circular financing between chipmakers and model labs is clever structuring or an accounting Ouroboros. Finally, the philosophical hangover. We react to Elon Musk's Economist interview and his claim that money stops mattering within a decade, pressure-test his deflationary argument against MV equals PQ, and ask why every science fiction author who ever imagined artificial superintelligence wrote a horror story. Plus Anthropic's positioning ahead of a possible IPO, the distillation and copyright fight with publishers, the rare books being unbound and shredded to feed training data, and where value actually accrues if models commoditize. Energy and molecules, or something else entirely. Subscribe for weekly deep dives on AI infrastructure, credit markets, semiconductors, and the money moving underneath the entire AI build-out.

July 24, 202616 min

Why Jamie Dimon Won't Buy Stocks OR Bonds Right Now

Short interest in the S&P 500 is sitting near its highest level since 2010, Jamie Dimon says he won't touch US stocks or Treasuries at these prices, and SpaceX is the ninth-most-shorted stock in the market ahead of its very first earnings report. So this week we're asking: why is everyone so bearish when the market is up more than 15% from the March lows? What did Alphabet's first-ever negative free cash flow quarter reveal about the real cost of the AI buildout? And when the five biggest hyperscalers are planning to spend nearly as much as the US military in a single year, who's actually going to fund it — and at what price? That last question took us straight to the bond market, where things look even scarier. Why are Meta, Oracle, and SpaceX's 30-year bonds trading 40-60 basis points wider just weeks after issuance? Why have 30-year Treasury yields held above 5.00% for the longest stretch in two decades — and is 5.00% the new floor instead of the ceiling? With a Fed meeting days away and Chairman Warsh's hawkish instincts colliding with the biggest negative CPI print since 2020, we dig into what the rates market is telling us about risk premiums across every asset class... and whether anyone wants to own anything right now.

July 18, 20261 hr 14 min

Ex-Morgan Stanley Bankers' "Yesteryear" HOT TAKES: Trad Wives vs. Career Women

We're talking about the buzziest --- and most controversial --- book of the summer: "Yesteryear" by Caro Claire Burke. It poses a question no one's brave enough to answer: are trad wives and career women fundamentally at odds? Or are they two sides of the same coin, minted by a bigger system that profits from their fight? As two Wall Street veterans recently profiled in Bloomberg for our new career as "finance influencers", we HAD to talk about the novel everyone is calling "rage bait", and we've got quite a lot to say. Fair warning: we spoil everything, INCLUDING the plot twist that has readers and critics alike up in arms. Why is a finance show covering a book about a trad wife influencer? The biggest names in this space, like Ballerina Farms and Nara Smith, are pulling in millions every year. The raw milk industry is a multi-billion dollar megalith expected to double in the next few years. And all of this is fueling a vertical of the creator economy that is growing in size (and scandals). What happens when a woman builds an empire by performing traditional acts of subservient domesticity on the most modern machine ever invented? We also turn the lens on ourselves, as moms, influencers, and educators --- where's the line between education and performance, and what responsibilities come along with influence?  Whether you loved this book, hated it, or refuse to read it on principle, we want to know what you think! Let us know in the comments...

July 16, 202647 min

How AI is Repeating the Exact Mistake that Bankrupted Enron | 50-Year Power Insider

With hyperscalers like Meta, Google, Amazon and SpaceXAI burning through cash, we decided to answer the question underneath all of it: what is this money actually buying? In this episode we start high level with a primer on the AI ecosystem or what Nvidia's CEO Jensen Huang calls the "five-layer cake" of AI — energy, chips, infrastructure, models, applications. We get into the vocabulary everyone uses and nobody defines: what a hyperscaler actually is, how it differs from a frontier model company like OpenAI or Anthropic, why Oracle only plays in one layer while Google plays in all five, and what a NeoCloud like CoreWeave is really doing when it borrows against its own chips. Then we get into the grid — all three of them — including how power prices get set, the difference between regulated and deregulated states, why Meta's $200 billion Project Hyperion campus in Louisiana needs enough electricity to power half of Manhattan in the summer, and why the new rule for data centers is essentially "bring your own electrons." We also dig into the tax incentives driving the timing of all this spend, and why states are competing so ferociously for projects that employ almost no one once the construction crews go home. Then we bring on an extra special guest: power expert. Ron Kelly, who spent 50 years in power and energy — as an engineer, at Calpine, and developing natural gas-fired power plants and solar plants all over the United States the country. He also happens to be Kristen's dad. His take is bracing: he's seen this movie before. Between 1995 and 2005, roughly 300 gigawatts of power projects were announced on the promise of the internet. 168 got built, 130 were canceled, the rest died, and Enron, Mirant, NRG, and Calpine all ended up in Chapter 11. Today's data center pipeline is about the same 300 gigawatts. Ron explains risks that could complicate the build out necessary to get all the needed power infrastructure online: the interconnection studies, transformer backlogs — plus what he really thinks about the security of the largest machine humans have ever built. Connect with Ron at   / ronald-kelly-pe-mba-3587a718  

June 14, 20261 hr 12 min

Mindy Kaling's "Not Suitable for Work": Our Hot Takes on the Show About Investment Banking in NYC We've Been Waiting For

Send us Fan Mail Mindy Kaling's new sitcom "Not Suitable for Work" just dropped, and we have thoughts. We are two Wall Street veterans breaking down everything the show gets right — and wrong — about what it actually looks like to show up as a first-year analyst at a bulge bracket investment bank, navigate office politics (and romance!), and try to build a life in New York City on a salary that sounds impressive until you see the rent. But this episode goes way beyond the finance. We're digging into the bigger questions the show raises: Is the Gen Z "lazy" narrative fair, or are young people today actually working harder than any generation before them for a fraction of the opportunity? What does the clash between generations reveal about the tension between hustle culture and the new workplace? And when a show in 2025 depicts five young people meeting, dating, and falling for each other entirely without apps, is that wish fulfillment or an active campaign for something we've lost? We're also getting into the male-female dynamics, the nepo baby problem, the intergenerational clash between millennials and Gen Z, and what it means that the most cutthroat character in the entire friend group is a woman. Plus — what does it say that the show's most pointed commentary on AI lands not in the banking storyline, but through a struggling med-student-turned-actor being asked to dig the grave of his own profession? We LOVE reviewing books, movies, tv shows, and everything in pop culture from a finance aspect --- send us your ideas for what you want us to review next! Shop our Self Paced Courses: Investment Banking & Private Equity Fundamentals HEREFixed Income Sales & Trading HERE Subscribe to our Substack: https://substack.com/@thewallstreetskinny

June 11, 202623 min

How Google Front-Ran SpaceX with a Record Breaking $85 Billion Equity Raise

Send us Fan Mail While everyone's been fixated on the SpaceX IPO, Google quietly pulled off the largest equity offering in history—roughly $85 billion—and basically front-ran the entire market to do it. In this episode of The Skinny on Wall Street, Kristen and Jen break down why a cash-printing machine like Alphabet would raise money at all, and why they did it in the most fascinating way possible: a Berkshire Hathaway private placement at a discount, a common stock offering across Google's quirky three share classes, a $40 billion at-the-market program, and the structure that confuses almost everyone—the mandatory convertible.If you've ever nodded along to "convertible debt" but secretly wondered what the hell stock that converts into stock actually is, this one's for you. Kristen (the First Lady of Valuation herself) walks through exactly how a mandatory convert works—why the number of shares you receive is a moving target tied to the share price, how the conversion math plays out from zero to a 25% premium and beyond, and why Google layered on a capped call to claw back even more upside. Along the way, they get into book-runner drama, IPO fee structures, why Tesla loved these trades, and what it really signals when sophisticated issuers are dumping rich equity, rich volatility, and rich call skew onto a market full of bullish retail buyers.The bigger picture? This is the AI build-out narrative wearing a new outfit. With 100% CapEx deductibility on the table and a talent war driving nine-figure pay packages, the smart money is raising as much as it can, as fast as it can—and using the hype to do it on favorable terms. Tune in for a clear, no-jargon breakdown of one of the most interesting capital markets moves of the year. Want to go deeper? Check out our Investment Banking & Private Equity Fundamentals course taught by Kristen Kelley—20 years of Wall Street knowledge, yours for two years. Shop our Self Paced Courses: Investment Banking & Private Equity Fundamentals HEREFixed Income Sales & Trading HERE Subscribe to our Substack: https://substack.com/@thewallstreetskinny