How Prep School Prepares You For Wall Street

Updated: Nov 15, 2018

A longstanding funnel of nepotism exists in New England. It starts at an early age with a youth tennis lesson at The Country Club in Brookline. Next your parents send you to boarding school in Connecticut. Before you know it, you’re splitting time stinging corners for Harvard lacrosse and getting tapped by the Porcellian Club. All's well that ends well when you’re favored in the eyes of the Wall Street finding yourself under qualified, yet more than well prepared for Investment Banking.

Our friend John Lefevre, the mastermind behind @GSElevator, illuminated valuable life lessons learned during his time at prep school. Take 10 minutes to read this excerpt and learn how he went from Choate Straight to Hell. Trust us... it's more interesting than your instagram feed. (Note: we prefer the audible narrator’s version available on Amazon.)

A Felonious Mentality (Excerpt from Straight to Hell)

“You may have escaped from this situation unscathed, but in my eyes, you are nothing but a weasel.” My adviser, Mr. Cobb, has just burst into my dorm room to share this uplifting gem with me. He looks at me (my head studiously buried in a textbook), glances over at my stereo (classical music playing softly), and then just rolls his eyes. Had I not been fourteen years old, he probably would have made the jerk-off hand motion.

In all fairness, his presumption isn’t too far off. Just two minutes earlier, I had recognized the sound of his not insubstantial weight coming up the stairs, quickly turned off the game of

Maelstrom I was playing on my McIntosh, flipped open my chemistry book, and switched from Dr. Dre’s The Chronic to the Vivaldi’s Four Seasons CD I stole from my mom.

“Mr. Cobb, coming from you, I think I’ll take that as a compliment.” Fuck him. As my fourth form (tenth grade) adviser, he’s supposed to be my ally, my father figure away from home, the guy in my corner, and a guiding presence during these crucial, character-building early teenage years. Instead, he has looked for every opportunity to pick me off. And at this point, there’s nothing I can do to change his opinion of me.

I’ve just experienced my first major run-in with the Choate Rosemary Hall authorities. Coming back from class a few days earlier, I had decided to grab a seat in the dormitory common room and hang out with some immediately collapsed from my rather underwhelming weight. I looked down to discover that someone had broken off the leg and then reattached it in a way that made it appear structurally sound; it was a booby trap. Admittedly, my reaction was rather juvenile. I picked up the chair and repeatedly smashed it into the ground until it splintered and broke apart, leaving the room strewn with shards of jagged wood and pieces of foamy cushion.

That night, at our weekly dorm meeting, our housemaster, Mr. Gadua (whom we had nicknamed

“The Gimp”), inquired about the broken chair. “I need the person who broke the chair to come forward.” Of course, no one said a word.

The next day, I received a meeting request from my dean; someone must have ratted me out. I’m getting sent before the judicial committee. Not only am I facing a charge for breaking the chair, I’m also accused of a much more serious honor code violation for lying to The Gimp.

Boarding schools tend to get sanctimonious and self-righteous when it comes to issues of honor. My first instinct was to argue that I broke the chair in order to prevent other people from being injured. But that wouldn’t absolve me from the honor code violation. So I decided to keep my argument simple.

“In my mind, as it relates to a chair, it is impossible to break something that is already

broken. So when The Gimp asked us about the chair, I did not step forward, because I genuinely do not know who broke the chair.” Case dismissed.

Even at this impressionable age, I knew that I wanted to go to Wall Street. I had never really enjoyed obeying authority figures, especially the idiotic ones like Mr. Cobb or The Gimp. Besides the influence of watching the movie Wall Street on basic cable and reading Liar’s

Poker (and then Den of Thieves, The Predator’s Ball, and Barbarians at the Gate), my fascination with Wall Street really crystallized during my first year at boarding school.

I became captivated by financial markets, the men who mastered them, and the tangible benefits that came with it. This was only reinforced when all the parents came down from places like Greenwich for parents’ weekend.

The Wall Street dads were the cool dads with the sports cars and a propensity for profanity. They’d tell our dean we were spending the weekend with let us disappear into New

York City, where we’d take down a suite at the Waldorf Astoria and use the concierge desk to get us into places like Scores and Au Bar.

This is when I internalized the number one rule of life: “Rules are for the obedience

of fools and the guidance of wise men.”

From my experience, Wall Street generally attracts people with a certain

mentality. It then takes those people, breaks them down, and molds them to suit its singular purpose—making money. Priorities are relative. Concepts of wealth are relative. Expectations and standards of hard work and intelligence are relative. Morality and deviance are relative. Wall Street operates in its own reality. Assimilate or die.

In its own way, boarding school was great preparation for investment banking. Not only were the Wall Street dads different, so were their kids. They had a much more evolved perspective, at a much earlier age, than the rest of us—a certain confidence, a kill-or-be-killed mind-set, even a felonious streak when it came to authority.

They were the kids in the dorms who somehow managed to get a doctor’s note that allowed them to have a refrigerator in their room. (It turns out every investment banker knows at least one doctor who owes him a favor. Where else were we supposed to get the Ritalin?) Their parents not only let them break rules they didn’t think should apply to them, but

encouraged and abetted them.

Boarding students can’t have cars on campus? No problem, just keep it in the parking lot at the public library in town. Students aren’t allowed to have cell phones (it’s the mid-1990s)? Be smart; just don’t get caught. Let scholarship kids, or worse, do-gooder types follow the rules. Then come talk to me in twenty years. They make little attempt to operate within the framework of a “meritocracy” unless it suits them. Can’t break 1300 on the SATs because you’re a moron? No problem. Get diagnosed “learning disabled” and then take all standardized tests untimed. One friend and classmate got an 1100 on his SATs, which, despite his being a legacy applicant, obviously wasn’t going to get him into Penn. A doctor’s note later, he was retaking the test untimed. Instead of spending four hours in a gymnasium with strict proctors looming over him like the rest of us, he had an entire week in a private classroom with minimal supervision, allowing him to covertly save vocabulary words, analogies, and math problems in his TI-82 calculator so that he could correct any mistakes the following day. A 1400 on the retake, which is still embarrassing under the circumstances—that’s like only netting $50K on a an insider trading scheme—got him off the Penn wait list, and now he works for a hedge fund in London and drives a Ferrari. Granted, he bought it used for less than the price of a BMW 5-series and works in a mid-office capacity, but none of that registers with his Facebook friends. He was

born on third base and scored on a wild pitch, but at least he can convince his friends (and

himself) that he hit a triple and stole home.

The ends justify the means; that’s an important concept to understand if you want to be

successful on Wall Street, and is one that boarding school taught me well. Being a young, naive kid from Texas, it took some time for me to grasp this mentality, but I caught up pretty


By junior year, I was the one with the Sega Genesis and TV hidden in my closet on top of my minifridge. I also learned other key trading-floor skills: bullying, hazing, and the art of a great


One night, a kid who lives across the hall from me leaves his room to go take a shower; he’s one of these dopes who showers at night right before lights-out in order to save time in the morning. Shower pranks are fairly standard. Someone will steal their towel, or lock them out

of their own room, or both. That’s boring. It’s happened to this kid so many times that he practically showers with one hand on his towel.

Knowing that we are both studying for the same calculus exam at 8 A.M. the next morning, I go into his room, take his calculus textbook and binder full of notes, stuff them into his closet, and then lock the closet door by looping his Kryptonite bicycle lock through the door handles and leaving the key inside. Then, for good measure, I also lock him out of his room.

He thinks that’s the joke— that someone has locked him out of his room while he was in the shower. No big deal. He walks downstairs in his towel and asks the housemaster to come up and let him in using the master key. It’s only about fifteen minutes later, presumably when he sits down to study, that he realizes that his books are missing and there’s a Kryptonite lock on his closet.

Now he has to go back downstairs and explain the situation to our housemaster, who has to call campus security, which then has to summon someone from the maintenance department to come up and physically saw off his closet door, a process that eats up two hours of prime study time.

Although they had their suspicions, no one was ever able to determine who the culprit/mastermind was. I’m pretty sure I beat him on that calculus test. My transformation from a young, naive kid from Texas was coming along. I was usually on some form of restriction or probation, and always under a cloud of suspicion. But I was developing an appreciation for absurdity and an ability to adapt quickly to the situation at hand.

The two come together one memorable spring weekend afternoon. I am sitting in my room, which faces away from the quad and out across the parking lot to the junior varsity tennis

courts. The parking lot is surprisingly full, as are each of the courts, with players and spectators. There are more parents than on a typical boarding school sports Saturday, which means it’s a home match against a nearby day school.

I’m a decent tennis player, but I never bothered playing in school. Being on the golf team was way more fun. With a dozen or so guys and only one coach, it was impossible for him to supervise all of us. Along with a few friends, our objective was always to play well enough to make the team and then never well enough to qualify for the top seven who would travel on match day for the tournaments.

A few times a week, we’d bus over to the Farms Country Club and play nine holes. Coach DeMarco would watch everyone tee off and then play his way up through each pairing so that he could watch and assess all of us fairly. We always made sure to be among the last few groups off the tee. Once our coach played a hole with us, we had six or seven uninterrupted holes to drink the beers we had stashed in our golf bags—and then throw the empties away on the eighth hole.

So here I am idling in my room having intentionally missed the golf tournament. For whatever reason, I decide to amuse myself by placing my speakers facing out my open windows and in the direction of the tennis courts. Snoop Dogg’s Doggystyle. Track 7. Volume up. Play. Snoop kicks off “Lodi Dodi” with a gentle reminder to his detractors that they are welcome to fellate him.

The sound is felt and heard with immediate effect. Most of the spectators instantly turn and face the dormitories looking for the source of the disruption. I crank up the volume almost to the point of blowing my Kenwood speakers. All match play soon grinds to a halt; I’m not sure if it’s because the music is so distracting, or if they simply can’t hear each other recite the score. That’s when I see the tennis coach, Mr. Goodyear, frantically scanning the windows. This guy is so stiff that he wears bow ties on weekends. He drops his clipboard and breaks into a full sprint toward the dorm complex.

Fuck. What I’ve just done is petulant, immature, and, worst of all, indefensible in its stupidity. I probably only have about thirty seconds to figure a way out of this. I dive away from the windows, strip naked, grab my towel, and sprint out and down the hallway toward the showers, leaving the music blaring and making sure to lock my door on my way out. I stay in the shower long enough for my heart rate to normalize, and then dry off and head back to my room.

Mr. Bowtie waits at my door. He’s hounding one of the security guys, who is fumbling through his massive key chain trying to find the master key for our dorm. Goodyear sees me coming toward them and screams, “Is this your room? Open the damn door.” “It’s not locked. I never lock my door.” I’m cool and relaxed. With the speakers facing out the window, we can hear each other perfectly, although the walls and floors are shaking like we’re backstage at a concert.

As soon as they get in, Goodyear goes right for the plug. I’m quick to point out that this has all the markings of an ill-conceived prank— someone has clearly taken advantage of the fact that I trustingly left my door unlocked while I was in the shower. “I don’t know who could’ve done this, but everyone pranks everyone around here.” Bowtie slinks off disappointed; he’ll have to wait another day to bring me down. Unbelievably, the security guy winks at me; he knows who’s boss.

One of my most important life lessons came senior year: Two different English teachers have tasked my housemate and me with the identical essay assignment on Beowulf. What starts out as innocent and sincere brainstorming quickly escalates to us staring over a laptop crystallizing our ideas together. We sit there for the next couple of hours, casually talking and taking turns typing. The end result is phenomenal.

A week later, I get another summons from my dean; once again, I’m being sent before the judicial committee, this time charged with cheating, an offense punishable by suspension. If you get suspended during your senior year, you have to inform the colleges that you’re applying to—basically I’m fucked.

The verdict comes back with a unanimous 5–0 vote in favor of probation for my codefendant and a 5–0 vote in favor of suspension for me. He is a two-sport varsity athlete and I’m an underachieving scumbag whose own adviser failed to support him at the hearing. There’s no justice in this world—a valuable lesson to learn at a young age, especially if you want to end up on Wall Street. I’ve seen some of the best traders and sales guys get fired at the expense of worthless assholes. Who you know is as important as what you do and how you are perceived is more important than any reality.

Knowing that the dean of students, who is also my English teacher from the previous year, has a soft spot for me, I take the unusual step of appealing the unanimous decision. I make a compelling argument that this is simply an instance of unauthorized collaboration, as opposed to outright cheating. The following day, my suspension is overturned, making me the first and only case in Choate history (that I know of) where a unanimous judicial committee decision has been overturned.

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