screaming toddlers, and my dad, Edward, a dentist, whose office was located on the ground floor of our house (how’s that for a commute?).
Our town was a quiet suburb about forty minutes north of Manhattan, consisting of 1970s split-level houses laid out along quiet, tree-lined streets, on which minivans carrying soccer-uniformed children drove by. It doesn’t get much more typically suburban than Dobbs Ferry, New York.
For most of my childhood and teenage years, right up until college, I led a wonderfully normal life. In the winter, we went skiing. In the summer, my parents shipped the four of us off to summer camp. I begged my parents to take us to “splinter park,” a park made entirely of wood, even though every visit consistently resulted in hours of painful tweezer removals. I brought home the chicken pox, and I graciously shared it with the entire family—even Arielle, who was only six months old at the time. And I attended the local Ardsley public schools, dutifully singing the Concord Road theme song every morning, until I switched to Horace Mann School later on.
I guess you could say that I was always a bit of a go-getter. I took piano lessons and somehow negotiated to spend the majority of my lessons singing, while my teacher played the piano. I ran cross-country and had my parents drive our car alongside me on the street so I could feel the pace I needed to run to make the varsity team. I acted and sang in school plays, community plays, summer camp plays—in any show that would have me, really. In high school, I expanded my interests. I became really passionate about studying and singing opera, and I joined the varsity fencing team, where I eventually became captain. I studied really hard in school, got good grades, and in 1999, despite having no special connections or advantages, became the very first member of our family to attend an Ivy League college, when I was accepted to Harvard University. To this day, I remain the only member of our family who has actually graduated.
People always ask me, “How was it growing up with your brother? Could you tell he was going to start a huge company back then?” The answer is a plain and simple no. We were a totally normal, happy family. Besides, don’t count the rest of us out yet. I have a feeling we’ll all be working for my youngest sister one day.
Fast-forward to April 2003. I had spent the majority of my time at Harvard studying psychology and singing with my beloved a cappella group, the Harvard Opportunes—and now my time at Harvard was ending.
My friends and classmates showed how it should have been done. In those final frenzied weeks after spring recess, every lunch, every party, every dash through Harvard Square was filled with happy, excited people—people with plans, lots of plans. And all those lofty ambitions and epic next steps could be summed up with names: McKinsey, Goldman Sachs, JPMorgan, Deloitte. It seemed everyone was heading to Wall Street or K Street to work in banking or consulting. Conversations with friends had become little more than summaries of future résumés.
At some point, the conversation would turn to me. “So, where are you heading, Randi?”
I would smile and look apologetic. “I haven’t quite decided yet. I’m thinking of something in the creative industry.”
Often these words produced only blank stares. Most of the on-campus recruiting at the time was done by consulting and investment-banking firms, so perhaps it hadn’t occurred to my classmates that other types of work existed and that one might even find those other types of work rewarding. (The shock!)
In any case, I wasn’t deterred. I had no interest in quantitative analysis or statistics, and the idea of gazing at spreadsheets all day bored me.
Several weeks before graduation, I began hunting for openings at advertising and marketing companies in New York. At one point, my dad excitedly told me that one of his patients worked for J. Walter