For Fun, My Career Origin Story

I just feel like writing a personal story. If you are here for the links or Money Angle feel free to skip ahead. No hard feelings.

When I was at Cornell I spent my first 3 semesters lost. I got bad grades. I tried on majors like you try on sunglasses. Computer science, sociology, psychology. I was fortunate that my mother worked at a bank so during the summer between freshman and sophomore years I interned in NYC, commuting back and forth from my hometown in Hazlet, NJ.

I did monkey work. Like mailroom clerk stuff. But the experience exposed me to traders. They were almost mythical. First of all, I heard they made lots of money. Secondly, they worked in a glass trading room surrounded by monitors and segregated from the rest of us in the “back office”. And the thing that impressed me the most — they got free lunch delivered straight to their desks. I was young and broke with no direction. This free lunch thing was apparently an incalculable perk to my small imagination.

So when I could, I would wander into the room and talk to them. They seemed so smart. They had opinions about everything in the news. They seemed to speak another language. I wanted to be like them. So I decided I would go back to my sophomore year and take economics courses. And since I was lazy, it helped that it only took 8 courses to complete the major.

The major was easy. I took a non-quantitative path and just needed to bullshit my way through those little white booklets with the blue lines. I seemingly had a gift for this as I managed to get nearly perfect grades for the rest of my time in school. All the while, not really learning anything. (This approach remains one of my greatest personal regrets. It’s an insecurity that unabashedly influences how I raise my kids.)

So senior year arrives. It’s 1999. Most of my classmates want to be investment bankers and .com stocks are IPO’ing daily and popping 100%. Everyone is daytrading. I skipped class and traded a few single stocks myself with the $600 I had to my name. Leftover cash I was given from the Red Cross when my friends’ and my apartment building burned down (shout out to my fellow “Refugee All Stars”). I didn’t have a process but I got the bug so I enrolled in an investment class in the Hotel school.

When the semester ended, I convinced the professor to let me be a TA and he put me in charge of basically running the class. There were 2 smart French PhD students who were my assistants. Professor Avner Arbell let me lecture a hall of 175 students for 15 minutes of the 75-minute class twice a week. I’m going to CNNFN.com every morning, printing out headlines or charts to be used on the overhead projector, then proceeding to make up a story of how it relates to something in the course. It’s so outrageous when I recount it. These students were paying to sit through nonsense.

So what happened? Well, as I was forced to prepare for these lectures it was the first time I did any real thinking. I was motivated by fear of being a fraud. Which I was. I was sincere but still a fraud. I must have done a good enough job because these students started to think of me as an authority. Which would lead to being asked questions, which led me to more research. And as I was working through all of this, two observations came together. One was I wanted to go into sales and trading, not banking. I heard about banking hours and being lazy I simply ruled that out. But the second observation was I enjoyed thinking about how macroeconomics seemed to relate to price. In hindsight, I think that link is so low resolution it’s a useless way to think about trading markets, but at the time it gave me the sense that if patterns existed they should be able to be exploited for money as easily as an ATM.

And so I started thinking of myself as a markets guy. Not a sales guy or banker type. I read Liar’s Poker many times over. I can see you cringing for me. So when I was walking around the career fair and I saw a guy at a booth with dice and cards I was intrigued. He wasn’t being flocked by sycophants in ill-fitting suits. And as I walked past a bit slowly he moved in with his pitch. Trading as a game. Odds and bluffing. Language that had nothing to do with “work” as I had conceived it. This was the language of fun. So I went for the interview. Lots of math questions. I got most of them wrong. But I asked him a simple question that may have changed my life. “What can I read that would make me better at this?”. He responded candidly. The first chapter of Getting the Best of It by David Sklansky. And so I read it over and over.

Whether it was mercy or perhaps he liked my question I don’t know, but this guy invited me to another interview. Little did I know that options markets were sizzling in the midst of the retail frenzy and this rep from Susquehanna just needed some warm bodies to stand in the pits and pick up the cash. And as luck would have it, the questions were straight from chapter one. All of them. I aced the interview. In subsequent rounds, I was able to hold my own without an answer key and just like that I was to be thrust into the world of trading options. Something I could not have imagined a year earlier. And even if I was probably a below-average recruit (this is for Susquehanna standards…I’m not calling myself an idiot. More than half of their hires scored an 800 on the Math SATs…I was coincidentally in the 5% of traders in the NYC office whose verbal SAT was higher than my math), I’m proud to be a survivor of a game which has weeded out more than 99% of its participants.

There are so many lucky breaks in this story. So many it might infuriate me if I were a jealous type and I was reading it. I’m aware of all of them. I have a lot of insecurity about my history. I was lazy. Unserious. And yet one historical accident after another broke my way. At least professionally.
So how do I honor that luck? Trying to figure that out is subtly shifting my perspective.

How do you think about your luck? What lessons or warnings are in your own stories? If anyone wants to share their own, I’d be honored to read it. Learning people’s honest versions is so upliftingly humanizing I thought I’d just take a stab an ask.

Thanks for indulging some very Moontowery musing.