FROM HEDGE FUND MANAGER TO HEADMASTER
On the outside, I looked nothing like a hedge fund manager. My wardrobe was from Target, and it wasn’t that long ago that I replaced my used car, which was valued at less than my junior partner’s Bugaboo baby stroller. I lived in Cambridge, Massachusetts, and even though my apartment was in a renovated Victorian not far from Harvard Square, it was a one-bedroom rental. I’m not denying, however, that it was a major upgrade from the basement apartment I had recently shared with a roommate, which had the entire building’s plumbing alerting me when anyone flushed.
Before I was my own boss, I worked for a hedge fund in New York City. There was a dress code, and I did my best to comply, but I often took off my shoes and went barefoot in the office to be more comfortable. The bosses accommodated me because my ideas were also different, and they liked those. Once I had my own fund, I frequently went to the office in sweatpants and a T-shirt.
I became a hedge fund manager because I was highly ambitious and I loved analytical pursuits. I joined the investment world right out of college, knowing how much I enjoyed solving investment puzzles that required my brain. I looked at complex situations and then broke them down to their essence. Much of my childhood had been a quest for complexity—baseball stats, tactical video games, board games, and inventing my own entertainment because the board games weren’t complicated enough. Before I’d entered college, I had created and marketed an analysis of the top high school basketball players in the country. Analyzing a player’s prospects was an exercise in breaking down a series of complex factors. Naturally, I loved it.
I went to college at Emory University in Atlanta, Georgia, where I majored in economics and took a few finance and accounting classes at Emory’s business school. Economic concepts came easily, and the finance concepts even more easily, so when a few internships introduced me to the world of banking and investments, I was completely sold. I’d get to use my brain analyzing the most complicated situations; the money would be a scorecard; and if I made enough, then maybe I could stop feeling pain at the prospect of splurging a dollar for a candy bar.
By twenty-seven, I was running my own investment firm, Flagg Street Capital, named for my beloved elementary school. I was in Stockholm, Sweden, talking to a room full of potential investors when one asked me, “You’re bright and enterprising. What will you do when you get bored with this?” Such a question presumed a success I didn’t at all take for granted, which perhaps threw me off. I answered without thinking. “I will help start a new country in Africa.” This generated more laughter than dollars.
Now, at thirty-two, I was nowhere near as wealthy as my hedge fund friends, but my savings allowed plenty of opportunities for enjoying my life. By most standards I was a huge success, but in my judgment I was a failure. I’d expected to become one of the elite performers on Wall Street, the next Warren Buffett, but undeniably I was not. I had my clear strengths in analysis, but I also had weaknesses. Sometimes, I allowed emotions to infringe on decisions. The hedge fund industry was an ultracompetitive world of intellectual superstars, many of whom had and most likely would continue to surpass me. I had not become the best, and the money was no consolation.
I decided to close Flagg Street Capital, give back all our investors’ money, and put my talents to a different use. The years since college had done nothing to lessen my ambition and ease my need to create something truly special.
How cliché is the story of the successful businessman who makes a lot of money, feels guilty, and suddenly grows a charitable heart? Well, that wasn’t me in any respect. I didn’t feel guilty; I was just unsatisfied with my meager accomplishments. Nor did I suddenly grow a heart. My mother had instilled in me a large one. For better or for worse, I was endowed with an often-painful weight of empathy. I’ve felt it for as long as I can remember, and I’m sure that’s because it started in my early childhood. In fact, I trace it to the most influential events of my life, which actually took place before I was born.
My mother grew up in New Haven, Connecticut, with her two brothers as well as her parents, Ethel and Irving Dunn. Ethel was one of six children, along with Mae, Annie, Max, Henry, and Eva. While I would never meet any of them, they defined my childhood. In 1964, twelve years before I was born, Irving Dunn, her father, died of a heart attack. Four months later, my mother finished her piano recital to find that her mother, Ethel, had died while she was playing. Thus my mother was orphaned at sixteen.
In the years that followed, Mom’s aunts and uncles died off in rapid succession. A story my mother told me when I was young summed it all up pretty well. Just a handful of years after being orphaned, she was studying at Clark University in Worcester, Massachusetts, the town where she would meet and eventually marry my father. She was at my father’s house one night during their courtship when she was told her brother Bill was on the phone. She picked up the phone, terrified. Bill started the conversation with “Don’t worry, it is only Uncle Max.” Only Max! As in, this time it was only Max who died. He was an uncle whom my mother truly loved. But Bill wasn’t being cruel. His saying, “It is only Max,” was because he didn’t want her to think that something had happened to their brother, Eli.
Then there were the letters. My mom wrote letters to my older sister, Beth, and to me, so if she suddenly died, we wouldn’t be left without a good-bye from her. We wouldn’t be fated to the sadness she still bore decades later after so many sudden deaths with no good-byes. Unfortunately, she told us about the letters when I was still very young. She believed if she were to die, these letters would be comforting. But I was a child, and this was a real miscalculation. I didn’t want to think about a letter if she died, because that made me think about her dying. Even as a child I’m sure I saw that the letters were an expression of my mother’s own pain.
To the young son who saw his mom cry for loved ones, the heartbreak of her losses caused a permanent scar that’s still as sensitive as an open wound. I can barely stand to write the story even now. The world has so much death and loss and pain and sadness. At the same time, the world has people like my mother, who balanced her heartbreak with an optimism she shared with me and with others lucky enough to know her. She is driven by heart—damaged no doubt, but also 100 percent committed to live to her fullest, even if that means risking more pain. More than anything else, even in my youth I realized that my mother was vulnerable, people were vulnerable, and the more vulnerable, the more human they were to me. When I see their vulnerability, I project my own fears for them; I project their sadness.
With Flagg Street Capital closed down and nothing holding me back, I wanted a project that satisfied my ambition and engaged my empathy. Somaliland was never far from my mind; and in its postwar condition, it certainly needed help. So I called my uncle Billeh.
We decided to take a two-week trip to his homeland. There we met people he knew, and I committed to starting a great school to develop the future leaders of the country. It was an ambitious goal but also one in which I’d be helping children who desperately needed an opportunity.
It is not lost on me now that helping needy teenage kids, many of whom have suffered terrible tragedies, was an expression of the sad little boy in me trying to help his own orphaned mom.