The Wall Street Skinny

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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!
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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.

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We'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.
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In 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.
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No 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=oF8tiwyuwvthXM26

Shop our Self Paced Courses:
Investment Banking & Private Equity Fundamentals HERE
Fixed Income Sales & Trading HERE
Subscribe to our Substack: https://substack.com/@thewallstreetskinny