Wall Street Reflections
"After I make $X, I'll just get off the tiger."
Finance is an industry where you’re perpetually proving yourself: win lead left, beat out other bidders, get the highest valuation for your clients, close the deal.
It's very dynamic work. My first day on a live deal, hundreds of emails poured in every hour. It’s understood analysts reply immediately or we might lose them (“strike while the iron is hot”). While collecting bids and assessing interest, I’m absorbing as much information as I can. Then, at the end of the day, the Managing Director says, “We don’t have enough interest. It’s bad optics on the firm. Go out and shake the trees!” —as if twenty-year-olds could conjure bidders out of thin air.1
Banks want twenty-year-olds for foot soldiers, not overhead. The issue with choosing investment banking right after a liberal arts education is that I had just spent four years practicing how to ask critical, open-ended questions. A finance recruiter once told me they spent about $50K per recruit, on candidates that last 2-3 years max. Banks need young people to think in answers, not questions.
At the junior level, I had very little visibility into what was actually going on. I got the sanitized version. More knowledge can make people more doubtful, so senior bankers have an interest in keeping their analysts (foot soldiers) single-minded.
Then there’s the cachet of working in the “front office” (revenue generating) versus “middle” or “back office” (cost centers). I wanted mergers and acquisitions (M&A) because sales and trading (S&T) felt too ballsy (shorter hours, higher intensity). And sell-side products were too niche: Capital Markets (ECM/DCM, LevFin) didn’t seem to cultivate as many transferrable skills.
Senior fall once I signed the offer, school became just another hurdle. As someone who once romanticized college as an intellectual journey to enrich society and engage in the life of the mind, I quickly adopted the same mentality as my bank-bound peers: “Here to pass, not to learn.”
After Superday, when offers are doled out, banks assure you they’re improving work-life balance and understand young people have lives outside of work. But once you’re in, they expect 24/7 responsiveness.2 And since bonuses are based on results, not how we got there, the most demanding people are the most successful. In my short time as an analyst, I saw junior bankers get dragged from toilets, showers, hospitals, holidays.
I once got a call at 5am from a VP: Send me [this thing] right now!
Me: I already sent it to you.
Him: Whatever, send it again.
Some markets are so niche ("exotic instruments") only a dozen banks make markets in that security. At that point, you’re no longer trading on the intrinsic value of the underlying asset: you're playing your opponents, not your cards.
Wall Street is one big poker game, and everyone is competing to get to the last table because of how comp is structured. Heads of product and industry groups run their own fiefdoms, with hundreds down the chain of command. A major departure means a dozen mid-level bankers may follow because they could be on the chopping block. From the outside, it’s like watching a stack of cards fold in slow motion.
Banks need young people to think in answers, not questions.
Banks are enormous beasts; I don't think any one person has visibility into how the whole thing actually works. A lot of people enter the industry thinking, after I make [number], I’ll just get off the tiger. But that’s not how it works.
Other people are there because they’re the blue-blooded Connecticut boy whose dad is a partner on the buy-side. My neighbor in the bullpen was a guy who did coke recreationally at his desk at 8am. Another could do Excel with his eyes closed. In a menagerie like that, not a single day that passed was boring. Between late nights and early mornings, I found poetry in the absurdity and met lifelong friends along the way.
My fondest memory from this time was watching the sunrise from an MD’s office. I remember tracing the Manhattan skyline, lights of the city never extinguished, onto the silhouette of buildings that looked like crooked teeth in the early morning sun.
In a fleeting moment of clarity, I drew strength from the thought that this too would end. But there from my Midtown desk, I was trapped in the belly of a great capitalist machine—with the twisted satisfaction that the machine was churning with me inside.
Above: One of us is now runs low-latency trading at Citadel, and one of us made a kid’s bear toy whose work has made her a thousandaire. Life works in mysterious ways. 🤷🏻♀️
If anyone’s curious what working for the venerable Andy Capitman was like, here’s an excellent first-person account from Jonathan Knee, now senior advisor at Evercore. My favorite line: “I found the company represented by the point with the greatest distance below the line and declared it the biggest bargain in the global poultry firmament.”
Just search “bed check” on WSO. Publicly known examples from Barclays in 2017 and Moelis in 2018. It’s entirely possible the culture has improved since my time as an analyst.