From Goldman Sachs Trader to Parking Lot Striper

3 months ago I was trading a $20 billion dollar derivatives portfolio for Goldman Sachs, now I am painting parking lots. What happened?

90 days ago I was a vice president in Goldman Sachs’ Equity Division in NYC. Running a derivatives trading book of over $20bn dollars in notional value that had made Goldman hundreds of millions of dollars in profits.

Yesterday, I installed 90 parking stalls and 7 directional arrows in an industrial lot for a roofing company in South Florida. Spraying solvent-based paint while dodging tractor trailers and tar trucks in 100° heat.

The craziest part of it all is that this was all my own choice…

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Back story

“Because, that’s where the money is.”
Willie Sutton, when asked why he robbed banks

To understand how I got to the above we need to go back in time over a decade ago. I came to Goldman out of extreme financial insecurity. My parents had lost their house in the global financial crisis while I was still in high school. I remember juxtaposing the fights (over money) at home with the headlines of the wily traders on Wall St. who were making hundreds of millions of dollars.

A few years later, I was a bench-warming, undersized basketball center in college whose herniated L4 & L5 vertebrae evaporated any far-fetched hoop dreams I had left. I needed to figure out what to do with my life. After doing significant amounts of research and cold-calling, I hopped on a bus to New York City and showed up on Goldman Sachs’ doorstep unannounced and asked for an internship.

By some mix of gusto and good fortune, I got in as a sophomore intern at GS, returned for my junior summer, and secured a job as an analyst on the equity swap and ETF sales desk. Within two years I taught myself a quantitative and coding skillset, was promoted early to associate, and became the first salesperson to have developer access within Goldman’s history.

I then made the rare switch from a sales to a trading role, developed and ran a trading book that made GS hundreds of millions of dollars in PnL over the years, all while navigating one of the most hyper-political and competitive workplace environments in the world.

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In need of change

My first itch for change was a reaction to how extreme of a place New York City is. Two years ago my wife and I moved from Brooklyn to Jersey City after we began trying for a child. It was the more affordable and family friendly option. We had a home birth, and I caught my son in my own hands in a 900sqft 2br apartment that cost us $5k a month (a 30% discount to living across the Hudson in TriBeCa).

At a combined TC above half-a-million dollars we were firmly NYC middle class. And after doing the math on top-tier childcare, it made more sense for my wife, a design director at a branding agency to leave her job and stay at home to raise our son. The fact that quality child care could easily outpace a senior position salary in NYC is just one facet of the financial squeeze one feels while living there. I used to joke that it costs to breathe in NYC, but the unfunny side is that despite the high expense we were rewarded with diminishing return on value.

The Paulus Hook neighborhood we lived in was relatively quiet; but I would still worry if my wife and son walked too far West or North, let alone if they went into NYC. I recall a month before we left a string of women being punched in the face by random strangers on the sidewalk. During that same time rapes and robberies were increasing year over year.

Nobody wants to live in a place where they fear for the safety of their loved ones. I witnessed the NYC metro area decaying into a large no-go zone, while cost of living ratcheted higher. It became clear to me that a change of location was in order.

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In need of challenge

“Men destroy each other during war; themselves during peacetime.”
Nassim Nicholas Taleb

With years of growth and success under my belt, I had become very comfortable, too comfortable, in my role at Goldman. By my last few years, I could perform my job only half-paying attention. This afforded me time to read and research my own idiosyncratic intellectual pursuits, but also left a feeling of something missing.

A month before I decided to leave was the 10^th anniversary of David Graeber’s article on Bullshit Jobs. I do not agree with much of Graeber’s thought (he is a Marxist) and I will save a full review of Graeber’s work for a later post. But suffice it to say that I agree with his thesis that dedicating a human life to an unserious, unchallenging role whose output had little-to-no-effect to himself or his surroundings provides a certain cruelty to the soul. This cruelty is especially nefarious because it is so hard to explicate and counteract.

Though I wouldn’t call the derivatives trading role at Goldman a bullshit job exactly (again a story for a later post), I couldn’t escape a voice that would whisper in my ears on Sunday afternoons that what I had decided to do with my life was a low evasion of human potential.

Perhaps I was being overly romantic, naïve and just a tad hubristic. But the question haunted me: If I could have this much success in this role and this city only dedicating a portion of my focus and effort, what could I be doing for myself elsewhere?

In college I had read Nassim Taleb’s works and his praise of risk takers and entrepreneurs stuck with me. I’ve had the opportunity on multiple occasions to have dinner with Taleb through a coterie of finance professionals and friends in NYC. As much as he harped on how important personal risk taking was, the truth is that many of his closest followers were little more than corporate strivers and rat-racers.

I pushed them on how they could praise a man’s work while ignoring the core of his message. The evasions they provided were rote: they had families to support and social standings to uphold. These excuses always struck me as pathetic.

Why is everyone such a coward these days? The roles we were in were all safe and comfortable. Using family as proof of valor or cover for evading pursuit of something greater seemed particularly low.

Children learn from what they observe. How can someone teach his son or daughter to be honest, independent, and courageous if he never provided an example of it himself? If he never even tried.

Entrepreneurship is far from easy, and not at all ensured to succeed; but even a failed attempt is better than none. To quote John Taylor Gatto, “The hurt from getting beaten only lasts a little while, but the hurt from giving up without a fight never goes away.”

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In Need of Freedom

“War trains men to be free.”“
Friedrich Nietzsche

The more time I spent at Goldman, the more I felt the reigns of my own life had been taken out of my hands. Even working in a successful and checked-out role, I felt I had almost no personal autonomy.

Over the years, the strict in-office policy kept me away from sick family members. My job took hours of my day away from my son. And I was coerced into receiving faulty medical injections - all for a job that I wasn’t passionate about and to make money for people who didn’t care for me.

Goldman is an intensely political place. No matter how much money I made for the firm, nor how crafty and clever I was in arbitraging the equity markets – my fate rested on how well I played the game of politics. There were traders with less-than-half the PnL contribution I had who were paid over 3x what I made and were up for promotion ahead of me because they did the song and dance better than I. Whether pride or inability, I just couldn’t force myself to focus on politics and optics over results. And I felt this burn inside me.

Further, I had never done any other professional work. I didn’t know how to make money if it didn’t involve selling or trading equity products – something completely ethereal and with little-to-no impact on the things I was passionate about. The company line at 200 West was that we were providing a societal good by upkeeping liquidity in the capital markets. But could I honestly say I knew how to bring value to a community?

I felt neutered and incomplete in some way. Throughout history, humans have been able to make a living by providing tangible value for those around them. Was I so alienated from my own humanity and community that I couldn’t actually provide something concrete for them that in return could sustain me and my family?

There is a light that goes out in a domesticated animals’ eyes when it is finally broken. I had the unnerving feeling that if I didn’t go out and learn how to create value in a real way for myself and those around me – then I would be lost forever.

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The hunt begins

So what to do? My wife and I decided to break free. I had been toying with the idea of buying a small business for some time and was finally in the financial place to do so. We started a self-financed search fund (the fancy B-school term for a pool of capital looking to acquire a small-to-mid-sized business (SMB)).

We targeted South Florida – it was far away from NYC, we had friends and family there, and it’s fun, freaky, and free.

Our investment thesis consisted of the following:

• A B2B, services-based business

• Within a fragmented industry

• A simple business – a boring-old-business (BOB) preferred

• With an EBITDA between $500k-$2m a year

As one of my mentors opined: you have to treat buying a business like a business. And we did. We analyzed over 300 listings, signed two-dozen NDAs, and hired an intern and an advisor.

The expected time frame to complete a search fund is two years. It seems nothing short of providential that an alum from my college happened to land in my inbox a few months into our search pitching me on starting a franchise. I was incredibly skeptical at first, there was no way I was going to leave Wall Street to open a Baskin Robins. But we told him our investment thesis and he returned with a list of opportunities that fit what we were looking for near-perfectly (outside of being a turn-key business).

The first business on the list was 1-800-STRIPER, a parking lot striping franchise that had territory available right where we were targeting in South Florida. After a few months of due diligence, we decided to pull the trigger.

As I walked into my boss’ office to resign the last thing on my mind were the years spent on the trading floor, the achievements, and the prestige of the job. I thought of witnessing my son grow in just the first few months of his life. How I would never get to hold him as a newborn, nor witness his first words or steps again. Time is not something we can get back, and if I didn’t break free of this situation now, it would be just another chance that I never took.

So in three months time, my wife and I moved 1200 miles, took over 100 hours of training, and started our own blue collar business in the wilds of Florida. We are in an affordable and safe location. I am creating something tangible of real value - putting paint stripes in parking lots. I am in the driver’s seat of my own life and career. And that is how I found myself going from trading equity derivatives to striping parking lots in 100° heat.

I made a jump. It may be the most ingenious thing I’ve ever done or the most idiotic. Time will tell. But we did it, and to be honest, dear reader, that is what matters to me.

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