The Wall Street Skinny

Hosted by Kristen and Jen

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250

Latest episode

Jun 2026

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EN-US

About the show

Where Bloomberg meets Page Six. 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

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 MailMindy 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 HERESubscribe 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 MailWhile 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 HERESubscribe to our Substack: https://substack.com/@thewallstreetskinny

June 10, 202641 min

Spotify Executive: How to Become a $100B Company When Everyone Expects Your Product Free

Send us Fan MailWe've done the finance of Industry, the finance of Succession, the finance of Belle Burden's Strangers — but we've never done the finance of CREATORS. So when Spotify invited us to their Investor Day, we knew we had to sit down and ask the question every aspiring musician, podcaster, and Instagram creator is obsessing over: in a world where everyone wants to be a creator, how does anyone actually get paid?In this episode, we talk with Gustav Gyllenhammar, SVP of Markets and Subscriptions at Spotify, about the surprisingly complicated machinery behind every stream you play. Where does your $12.99 a month really go? How much does a million downloads of a song actually pay out? And how did a company born out of a piracy-ravaged Sweden convince an entire generation to start paying for something they'd grown up expecting for free? We get into the labels-versus-songwriters split, the rise of the independent artist, and the one number that explains why Spotify thinks it's playing a completely different game than the AI companies scraping the internet for content.Which brings us to the real tension underneath it all: as LLMs hoover up the work of writers, musicians, and creators everywhere, who's building a model to actually compensate them — and is Spotify offering a better blueprint? We dig into Spotify's philosophy on AI, why they waited so long to touch it on the music side, what "Time Well Spent" means when every other platform is optimizing for your attention, and whether the creators who power these platforms are about to get boxed out of their own economy. Plus: the new Universal Music partnership, the audiobook feature Jen has been praying for, and why a direct listing might be the most underrated way to go public.Shop our Self Paced Courses:Investment Banking & Private Equity Fundamentals HEREFixed Income Sales & Trading HERESubscribe to our Substack: https://substack.com/@thewallstreetskinny

June 6, 202631 min

SpaceX Just Rewrote the Rules of the Stock Market (And Most People Had No Idea)

Send us Fan MailIn this episode, we dig into one of the biggest market questions hiding behind the hype around mega IPOs: what happens to passive index investors when companies like SpaceX, Anthropic, and OpenAI go public? We ask why the VIX and major indices like the S&P 500 and Nasdaq look calm, while single-name stocks like Tesla are showing much higher implied volatility, and why the spread between index volatility and individual stock volatility has reached extreme levels. Along the way, we break down the dispersion trade, implied versus realized volatility, and whether upcoming IPOs could force investors to rotate out of existing AI, tech, and “Elon trade” names to fund new allocations.We also explore how changing index rules could reshape the market structure itself. Should a massive company like SpaceX be included quickly in the Nasdaq or S&P 500? How do float requirements, seasoning periods, profitability screens, and liquidity constraints affect ETF investors and passive funds that have to buy the underlying shares? We debate whether excluding these mega-cap IPOs would distort benchmarks, whether including them could create liquidity pressure, and how SpaceX, Anthropic, and OpenAI could change the relationship between passive investing, active stock picking, and index volatility.Finally, we ask whether today’s market setup is starting to echo the dot-com bubble, with bullish sentiment, a low put/call ratio, AI enthusiasm, and a wave of high-profile IPOs creating both opportunity and risk. Are investors buying call options like lottery tickets? Could the arrival of new public AI and space stocks drain capital from the Mag Seven, Tesla, software, and private markets? And as AI infrastructure companies become publicly investable, we question whether the real winners will be the foundational LLM providers, the tech giants, or the next generation of startups built on top of them.Shop our Self Paced Courses:Investment Banking & Private Equity Fundamentals HEREFixed Income Sales & Trading HERESubscribe to our Substack: https://substack.com/@thewallstreetskinny

June 3, 202642 min

Ex-Morgan Stanley Bankers: "Strangers" How Much Belle Burden's Husband Was Actually Earning

Send us Fan MailNo one is talking about the insane thing that's happened to Big Law partner compensation over the past decade — and how it stacks up against Wall Street.In this deep dive we broke down EXACTLY what's going on. What started as an attempt to quantify how much Belle Burden's husband — from the cultural phenomenon Strangers — was actually earning during their marriage, after he left Davis Polk and landed at an equity long/short hedge fund, turned into a full-blown investigation: how Big Law and hedge funds really make money, what the compensation structures look like, and who actually comes out ahead.We were positive we knew the answer. We were wrong.Here's what we're not going to spoil — but here's what's on the table:One firm reportedly offered $80 million over three years to poach a single partner. That's not a typo. That's hedge fund money… for a lawyer.The top firms are clearing eight figures per partner — and we name them.The Financial Times has reported some hedge fund traders are being offered 9 figures comp packages but how does it vary roles by role, firm by firm and year by year, We get into the lockstep model, the eat-what-you-kill brutality of the buy side, "two and twenty," and the math of who's really ahead at 25, at 35, at 45 — plus the quiet shift that flipped the entire game while almost nobody outside the industry was watching.📩 The FULL breakdown, complete with financial model if you want to see play with key assumptions lives on our Substack: https://substack.com/@thewallstreetskinny 🎧 Our original breakdown of Strangers: https://youtu.be/3fbWStK44P0?si=N5Qif1UhVxz06i7l🏛️ For the deal nerds — our Caesars Palace coup series: https://youtu.be/VKROBLck-RA?si=oF8tiwyuwvthXM26Shop our Self Paced Courses:Investment Banking & Private Equity Fundamentals HEREFixed Income Sales & Trading HERESubscribe to our Substack: https://substack.com/@thewallstreetskinny

May 27, 202651 min

Ex-Morgan Stanley Bankers: "Strangers" by Belle Burden Part 1 | Our Initial HOT TAKES

Send us Fan MailTwo weeks ago, one of the most powerful women on Wall Street asked us to weigh in on Belle Burden's bombshell memoir: "Strangers". As two women who've lived and worked in every world this book touches — from raising three kids in New York City to working on Wall Street to growing up in Massachusetts and spending summers on Martha's Vineyard — we're uniquely positioned to read between the lines of a story that's been everywhere from Oprah to every video in your feed.In this episode, we break down the full financial picture most coverage glosses over: the prenup that may have been the original sin of the marriage, the real numbers behind a Davis Polk associate's salary vs. a fund-of-funds partner's take, how much Belle's husband likely earned at Arden and Select Equity, the math on a $4M Tribeca apartment and a $5.4M Martha's Vineyard estate, and why "running up quicksand" is the only way to describe trying to build wealth on a W-2 in Manhattan if you don't have a wife who's heiress to a Vanderbilt fortune. We also dig into the power dynamics — the resentment baked into the prenup negotiation, the "make me a sandwich" moment, the affair with a sell-side banker, and why the cheating partner in these stories is almost never really about the other person.But here's where their take diverges sharply from Belle's own messaging: the real lesson isn't "know your finances" — it's something much harder. We argue that no amount of financial literacy would have changed Belle's story.Shop our Self Paced Courses:Investment Banking & Private Equity Fundamentals HEREFixed Income Sales & Trading HERESubscribe to our Substack: https://substack.com/@thewallstreetskinny

May 26, 202640 min

Hedge Funds Want the Equity in Your Home, feat. Tacora Capital Founder Keri Findley

Send us Fan MailIn this episode we dig into the state of the American consumer's balance sheet, which on paper isn't broke but is increasingly "boxed in." We walk through eye-opening Federal Reserve data: total household debt hit an all-time high of $18.8 trillion in Q1 2026 (up $4.6 trillion since pre-COVID), credit card balances peaked at $1.25 trillion with rates north of 20%, and while headline wages are up roughly 32% since 2020, real inflation-adjusted earnings have grown just 2-3% against housing, insurance, and grocery costs that have surged 60-80%. The result is a deepening K-shaped economy where homeowners are sitting on a record $17.8 trillion in equity, including roughly $11.6 trillion that's "tappable," but can't realistically refinance out of their 2-3% pandemic-era mortgages.That sets up a fascinating conversation with Kerry Finley, founder of Tacora Capital, about Home Equity Investment options (HEIs), a product profiled in a recent Bloomberg piece. Unlike a HELOC, an HEI isn't debt: an originator like Point Digital buys a percentage of the equity in your home for cash today (with a volatility haircut), takes no monthly payments, and settles up when you sell or refinance. Kerry breaks down a clean example using a million-dollar home with a $600K mortgage, explains why this product fits borrowers who can't clear the 750+ FICO bar for a HELOC (including 1099 and K-1 earners), and why the average returns on these instruments have been around 17% since 2015.We also explore why this isn't a 2008 redux, where HEIs fit in residential real estate's hyper-local landscape, and how the product might actually serve as a credit-curing tool for consumers carrying expensive card debt. Shop our Self Paced Courses:Investment Banking & Private Equity Fundamentals HEREFixed Income Sales & Trading HERESubscribe to our Substack: https://substack.com/@thewallstreetskinny

May 14, 202655 min

$53 Billion Hedge Fund Chief Strategist: The Next Market Shock Is Hiding in Plain Sight

Send us Fan MailWe sat down with Elizabeth Burton, the new Chief Strategist at Fortress, one of the world’s biggest and most respected hedge funds, to ask what actually matters most in this market — and her answer might surprise you.This is the same Elizabeth Burton who, back in 2020, made the call that inflation would be sticky, not transitory — while much of the market, and even the Fed, was still arguing the opposite. Now she’s back with another uncomfortable view: the market may be focusing on the wrong risks again. In this episode, we ask why the bond market matters so much, whether investors are too eager to believe we’re going back to a 2018-style world of low rates and easy returns, whether the panic over private credit is missing a bigger problem in private equity, and what happens if AI disruption doesn’t stop at software.We also get into the next sector that could be blindsided by AI, why the allocator world may become increasingly K-shaped, how the biggest institutions could fall behind if they can’t move fast enough, and what market risks keep investors up at night even more than private credit. Plus, Elizabeth tells us how she almost became a New York City beat cop, why Fortress is not the private equity shop some people think it is, and how she almost got denied insurance coverage after being accused of climbing Mount Everest.You do not want to miss this episode!!Shop our Self Paced Courses:Investment Banking & Private Equity Fundamentals HEREFixed Income Sales & Trading HERESubscribe to our Substack: https://substack.com/@thewallstreetskinny

May 8, 202624 min

Burry Left in a Hurry! The Loophole GameStop Could Use to Pull Off Buying eBay (10x its Size)

Send us Fan MailMichael Burry just dumped all his GameStop shares. eBay reportedly deactivated Ryan Cohen's account. And the $56 billion "takeover" GameStop pitched on CNBC? It would actually have eBay shareholders paying for most of it themselves. We're back to break down the latest twists in the GameStop–eBay drama — and why this deal is structured unlike almost any takeover Wall Street has seen.In this episode, Kristen walks Jen (and you) through the rollover equity mechanics that make this look less like an LBO and more like a SPAC, the precedent Bill Ackman set when he paid $10 million to get the SEC to approve his SPARC, and why levering eBay up at 7–10x puts the combined company at material bankruptcy risk over the next few years. We also get into why eBay might actually want a version of this deal (just not this version), and whether a private equity firm could step in with a cleaner bid, Shop our Self Paced Courses:Investment Banking & Private Equity Fundamentals HEREFixed Income Sales & Trading HERESubscribe to our Substack: https://substack.com/@thewallstreetskinny

May 5, 202617 min

GameStop Just Bid $56 Billion for eBay. What is ACTUALLY Going On????

Send us Fan Mail🚨 EMERGENCY EPISODE: GameStop just made an unsolicited $56 billion bid for eBay, and the math is NOT mathing. After watching CEO Ryan Cohen's bizarre live CNBC interview with Andrew Ross Sorkin (where he kept deflecting questions with answers like "it's on the website"), we hit *record* immediately to break this down.Kristen, our resident investment banking, PE, and M&A expert, walks through why this deal defies the laws of physics:The offer: $125/share, half cash, half stock — roughly $56bn totalGameStop's market cap: under $11bnCash needed: $28bn (GameStop has $9bn on hand + a "up to $20bn" TD Bank commitment letter)Combined company leverage: ~10x EBITDA (a massive LBO is typically 7x — banks don't do 10x)The $17bn equity hole: where is it actually coming from?We compare this to the Paramount/Warner Bros deal (spoiler: that one works because Larry Ellison is bankrolling it), unpack GameStop's curious 5% derivative stake in eBay, and explore the theories floating around — CEO comp package triggers, a possible "uno reverse" play to get eBay to bid for GameStop instead, and echoes of the Porsche/Volkswagen hostile takeover.Plus: Ryan Cohen's background, the dismissed Bed Bath & Beyond pump-and-dump lawsuit, and why no sovereign wealth fund has a strategic reason to write the check.Got a theory on what's really going on? Drop it in the comments.Want to learn how to actually run accretion/dilution analyses and tear deals apart like this? Check out our 35+ hour self-paced Investment Banking & Private Equity Fundamentals course, taught by Kristen.https://thewallstreetskinny.com/premium-self-study/Shop our Self Paced Courses:Investment Banking & Private Equity Fundamentals HEREFixed Income Sales & Trading HERESubscribe to our Substack: https://substack.com/@thewallstreetskinny