Why I Left Investment Banking to Pursue Social Entrepreneurship (and the Lessons Learned)

I took in the view overlooking Park Avenue in midtown Manhattan one last time, awed by the skyscrapers rising like massive towers out of the hustle of the surrounding streets. New York City always seemed alive yet serene from up here. Pedestrians, street vendors, and cars mingled like a well-orchestrated flow of ants below me, while the buildings mixed with sky in front of me. I took in the view, said a quick thank you under my breathe, then cut my ID card in half and left it on my desk as I walked out.

****

My pathway into investment banking began 5 years before as a nervous 19-year-old college student at Holy Cross. It was my sophomore year and I had just listened to some older students speak on a panel about their Wall Street experiences. They all spoke of long hours, difficult work, and constant tests to earn a full-time position.

One student had interned in the investment banking department. Of all the panelists, his experience seemed the most grueling — the longest hours and the most complex. I decided then that I wanted to give it a shot. I wanted to test my limits, learn from the best, and develop my skill set.

Over the next few months, I had countless calls to try to break in. Most ended the same way — you’re a nice kid, but you don’t go to a “target” school (i.e. Ivy League) and you are too young — maybe call me in a year. Nonetheless, I persisted and eventually a few alumni at a bulge bracket bank took a chance on me. I was told to be at Park Avenue for an interview in a week.

I remember frantically calling my parents, arranging transportation, and studying every moment I could find. I had a mock interview with an alum that included the phrase “don’t say that — you sound stupid” so I knew I had a lot of work to do. After a few days of constant studying and little sleep, my dad picked me up to drive to NYC.

As we drove closer, the city changed from a small speck on the horizon to a colossal mixture of iron and power. I was new to New York, so my dad showed me how to find Park Avenue, wished me luck, and watched from afar as I walked into a large black office building for my interview, engulfed by its tinted black windows.

I emerged hours later with a pounding headache and an unsure feeling. I had spent hours being peppered with questions by different interviewers trying to find a chink in my armor. I silently hoped I had done well enough to earn a spot.

24 hours later, while catching up on the school work I put off for the past week, I heard my phone buzzing and scrambled to pick it up. I saw a missed call from a NYC area code and called back immediately. Congratulations, report for your internship in June.

****

While my pursuit of an investment banking internship took up some time, it was only a small part of my liberal arts education. My days were spent studying, hanging out with friends, and volunteering in the Worcester, MA community. I was originally drawn to Holy Cross for its mission of educating “men and women for and with others” and this mantra permeated every facet of life at Holy Cross. From day one, it was ingrained in students that an education is not meant to only serve you — you are also meant to use it as a tool to serve the world.

In a sense, Holy Cross was a little gated utopia of academic rigor. Nestled on a hill, there was a constant flow of vans coming to and from campus, whisking students off to volunteer in various parts of the city — food banks, middle schools, immigration centers, and more. As a young civic minded individual, this was captivating and I wanted to know where I could make my mark.

Perhaps because my father is a Cuban immigrant who came to the United States as a child, I was drawn towards working with Spanish-speaking immigrants. While my childhood was sheltered, filled with rigorous academic study and a splattering of extra-curricular activities, I always knew that I had it good. Whether from a story told by my father, speaking with my grandparents through a mix of broken Spanglish, or watching my parents’ relentless work ethic, I knew that my opportunities were built upon generations of sacrifice. I threw myself into my studies accordingly.

Now at Holy Cross, watching those vans travel to and from campus, I finally felt like it was my chance to give back. All the studying, generations of sacrifice, and relentless work ethic would finally be put to use solving the world’s problems. When I was presented with the option to tutor refugee children who came to the United States by themselves, I jumped at the opportunity.

I remember pulling up to a tucked-away parking lot, walking up two flights of stairs, and seeing a number of nervous students there to meet us. I felt stupid and out of place in my Vineyard Vines pullover, but was quickly paired with a student who needed help with math as he studied for his GED (high school equivalency) test. Over the coming months, I would work with a number of students, teaching everything from algebra to the alphabet.

Needless to say, I quickly learned that I couldn’t change the world in one day. Back at Holy Cross, once the vans returned, students would huddle up and discuss our experiences while asking hard questions. How did it come about that a 15-year-old has only a 1st grade education? Why are so many former prisoners struggling to adapt to life outside the prison walls? Why are the local food pantries so busy?

Our college professors encouraged us to engage with the gritty reality of the world, to constantly question and search for answers, even if the answers were unsatisfactory. We learned that, while we weren’t changing the world, we were changing ourselves — challenging our world views, checking our assumptions, and growing in the process.

****

When June came around, I reported to NYC to start my internship. My parents helped set me up in a run-down dorm room where basically everything was broken (we had no A/C for the first, sweltering week and struggled with bugs the entire summer). I hung up my suits, met my fellow Wall Street intern roommates, and hugged my parents goodbye. My mom remembers feeling like she was leaving me to the wolves.

The next morning, my roommates and I donned our best suits and headed to our week of training. Despite traveling with an internationally renowned coder, who would spend the summer writing trading algorithms, and a varsity quarterback with a 4.0 GPA, we still managed to take the subway going the wrong direction and barely made it to the office on time.

This small anecdote could summarize my entire summer. Despite my best efforts, I constantly teetered on the brink of not getting a coveted return offer (i.e. not getting asked back for a second internship, thereby blowing my chance at a full-time job there after college). I thought I had taught myself basic finance and Microsoft Excel before I arrived, but nothing prepared me for the granular, 20-tab operating models filled with formulas and terminology I did not know. I distinctly remember changing a small formula in one cell and watching an entire 20-tab spreadsheet change from numbers to #REF before my horrified eyes. One fellow intern from an Ivy League school went so far as to say that people like me didn’t belong there. I smiled and said “we’ll see” but secretly wondered if he was right.

To make up for my lack of relevant skills, I tried to out-work and out-attitude everyone else. If a stapler was out of staples, I filled it. If the printer ran out of paper, I was on it. In the lead up to our final project, my last chance to prove my worth, I watched the sunrise from the office 2 days in a row and (in an embarrassing moment) caught myself typing random letters into the computer as I zoned out from sleep deprivation.

At the end of the summer, I got my return offer and finally allowed myself to relax. On the subway ride home, I fell asleep, waking up a stop too far — my return offer clutched tight against my chest — with a silly smile spread across my face.

****

After that summer, I left the Park Avenue board rooms and returned to the gritty reality of the world. The previous year, I had taken a student coordinator role with the tutoring program I participated in and expanded it to include a mentoring program and music lessons, but I still wanted to learn and do more. How did children wind up alone on America’s southern border in the first place?

Holy Cross offered a semester in Washington, D.C. and I jumped at the opportunity to get closer to the action. After finishing my Wall Street internship, I immediately drove to D.C. to spend a few months at an amazing non-profit that paired refugee children with pro bono legal counsel. While there, I would interview children to get their back story, attend hearings on Capitol Hill, and write a thesis on the laws affecting asylum applicants.

Compared with Park Avenue, my office was small and nondescript, overlooking a Domino’s Pizza. However, what the office lacked in flourish, it made up for with heart. The children were amazing, their stories heartbreaking, and my coworkers some of the strongest people I have ever met. Any cockiness built up from my time on Wall Street was soon squashed as I spoke with children targeted by brutal gangs, attended immigration court where a judge valiantly fought through a docket of 50+ scared children alone in court, and reflected on how cruel the world could be. After one particularly brutal case, I slipped out to the bathroom and cried.

Upon my return to Holy Cross, I was a bit shaken and trying to balance in my mind the two worlds I oscillated between — a world of big money and intensity on Wall Street and a world of tough realities but hopeful spirit in my volunteer work. This disjointed feeling of being caught between two worlds would continue as I completed another Wall Street internship then founded a non-profit to install technology labs at local educational programs.

Then, in a bittersweet moment, I graduated from college and plunged headfirst into my full-time role as an investment banker.

****

I clearly remember the first day, walking into a room of 200 other analysts, the best and brightest from around the world, everyone dressed in their sharpest suits. It was both terrifying and exhilarating. I reminded myself of the sacrifices made to afford me this moment and promised myself that I would make the most of it. I wanted to soak it all in, learn from those around me, and emerge a better version of myself.

It was harder than I expected. I had spent my college years volunteering when my co-workers had been knee deep in excel spreadsheets during their finance classes. The learning curve was steep and the time in the office soon blurred, with the work weeks turning into working weekends. I was running on little to no sleep, emboldened by adrenaline, naps in random spots, and well-timed coffee.

For the first few months, it felt as though nothing I did was ever right. We iterated until we reached perfection and I would leave the process licking my wounds and mentally noting all the mistakes I made so they would not happen again.

In my pursuit of success, my every waking hour was consumed by preparing Excel models, presentation materials, and responding to the endless flow of incoming emails. I made myself available 24/7, instinctively waking up in the middle of the night to respond to emails, even if I was only sleeping a few hours before heading back to work.

On those very late nights alone in the office at 4:00AM, I would lap the floor to stay awake. Looking over the darkened Manhattan skyline, I’d remind myself of the sacrifice it took to afford me this opportunity then plunge back into the work.

Despite the long hours and pressure, I was thrilled. Compounded by lack of sleep, the highs were high and the lows were low, and the moments when a deal got done or I mastered a new skill kept me excited. Since I was constantly making mistakes, I was constantly learning. I got access to incredible thought leaders, gained great mentors and friends, and, with an emphasis on the technology sector, was quickly learning the nuances of company strategy, valuation, and market analysis.

As the years progressed, I continued to learn more and got ever greater exposure and access. What once seemed so difficult, I was now teaching our new hires. I got an innate sense of pride when deals I worked on appeared on the front page of major newspapers and my performance reviews were great. I knew I was getting my footing. But something felt wrong.

I was getting great exposure, making good money, and had job opportunities coming in daily. However, as my friends left for private equity and hedge fund jobs, I felt like something was missing. While there is a pressure to continue down a path, I didn’t feel, at this time, that it aligned with what I wanted for my next adventure.

I called friends and mentors then spent countless hours sitting alone in the dark thinking (which probably creeped out the people visiting my apartment). I did a few interviews and researched a ton of jobs but nothing felt right until I sat down with a friend that had left to start a company. We occasionally met up to spitball ideas and he recommended that I write down 10 business ideas a day to see if anything stuck.

I had fun with it and, after writing down a series of admittedly terrible ideas, I thought of a few good ones. Then I noticed a trend — my best ideas, and the ideas that got me the most excited, appealed to both my sense of business and justice. They united the two worlds I had been oscillating between for the past few years. Would I be crazy to pursue social entrepreneurship?

After weeks of debating myself, I finally got the courage to try it. The night I told my manager I would be leaving my job, I couldn’t sleep. I stayed up telling myself I was insane — something must be wrong with me. But as time passed, and with the support of coworkers, family, and friends, I slowly started to realize it would be OK. The friends and mentors that I made would still be there, the skill set I developed would stay with me, and I had grown immensely as a person throughout my time on Wall Street.

My entrepreneurial pursuits will be focused on the education sector and the sustainable, ethical use of technology. I have the same terrified but exhilarating feeling I had all those years ago when I first started my investment banking job and look forward to the trials and growth the future has in store for me. While nobody has a crystal ball for the future, here are some lessons I learned along my journey thus far that I hope will serve me (and you) well.

1. Think critically

With the ubiquity of technology, it is easy to constantly be doing, rather than thinking. There are always emails to be answered, tasks to complete, and constant pulls on our time. As someone who was consumed by a 24/7 job, I didn’t at first allow my mind to wander, question, and analyze like I used to do after my volunteer activities. In the process, I missed important connections.

As time progressed, I began to get better at this and immediately began reaping the rewards. I was more thoughtful in how I went about my personal and professional life, finding ways to increase efficiencies and prioritize what mattered to me. Ultimately, I decided to do something different than my peers, a path I never could have fathomed without critical analysis of my goals, desires, and priorities.

I still struggle with this, but carving out time to think critically is pivotal to leading an attentive life.

2. Engage the gritty reality

As my Holy Cross professor once encouraged me, engage the gritty reality of the world. It is very easy to get caught in our own bubbles without engaging the world around us in a way that constructively challenges our world views. I’ve certainly fallen into this trap, especially when certain aspects of my world felt all consuming.

A basic human truth is that everyone faces a different reality than you. While it’s impossible to ever fully understand another person’s reality, engaging in thoughtful discussion and action can often lead to new perspectives, friends, and a greater sense of belonging. As someone who straddled the for-profit and non-profit world for years, I am shocked by how little people challenge their direct reality when they could learn so much from each other. Rather than judge, take a moment to think and engage.

Personally, the best lessons came when I least expected them. I learned lessons on mentorship, critical analysis, and relentless perseverance from my colleagues on Park Avenue. My non-profit colleagues taught me about teamwork, empathy, and self-care. I learned more about resiliency from a nine-year-old fleeing gang violence than I could from anyone else.

The world has a lot of lessons to teach, but it is up to us to break out of our bubble and learn them.

3. Be multi-dimensional

I am banking my future on this fact, so I sure hope it is right. I fundamentally believe that my volunteer experience made me a better banker and my Wall Street experience made me a better community leader. In my view, the thought leaders of tomorrow will be the one’s who challenged themselves to explore, fail, and learn today.

Our world is rapidly changing around us and the pace of innovation will likely continue to increase. With this change, comes new questions that will require multi-dimensional thinking. If you don’t know what I mean, here are a few examples: How do we think about bias in algorithms? What role does social media play in the information we consume? How do we balance privacy and data? How do we effectively deploy technology in education to keep up with ever evolving workforce demands?

I don’t claim to know the answers to these questions, but I do know that they will challenge us to think differently and engage in multi-faceted analysis. If the world requires multi-faceted solutions, should we not encourage ourselves to be multi-dimensional individuals? Breaking beyond our comfort zones and into new terrain is terrifying, but so very important in our ever-evolving world.

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While I am not sure exactly what the future will hold, I am grateful for all my past experiences and excited for the adventures to come. I look forward to asking tough questions, seeking answers, and growing in the process. If you’d like to chat, come along for the ride, offer advice, or bounce some ideas, you can find me on LinkedIn or my (newly created) Twitter account.

Education & Tech entrepreneur

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