My Journey (Part 2): Beginning my career in finance just in time for the financial crisis

I always wanted to be a banker like my father. As a little girl, I loved going to work with him. The whole process was spectacular: getting dressed up, taking the train into Grand Central Station, traversing the busy NYC streets to his office building, and staring out his office window onto the expansive skyline. I loved the energy of the workplace, watching the (mostly) men in suits and ties go in and out of meetings. It all seemed very important.?

I remember taking my father’s business cards, using Wite-Out? to remove his name, and replacing it with my own using a typewriter! I then moved up the ranks and asked the bank’s President for his business card so I could do the same—I was always ambitious! I made photocopies, cut them out, and handed them to people around the office. Even then, I knew that one day, I’d be a boss! However, I never thought I’d be leading a global analytics team.?

From that little girl to a young adult, my career ambition remained the same. Fast forward to college. I attended Cornell University as an undergrad, and after graduation, I spent a year in capital markets before achieving my goal of becoming an investment banker at Lehman Brothers.

Unlike many others, I enjoyed my time in banking. I was an Analyst working in leveraged finance. Focused solely on debt issuance, I liked that this team allowed me to work across many industries, including consumer, retail, gaming, hospitality, technology, media, and healthcare. I learned how to pick apart companies, to always read the footnotes of financial statements (that's where the good stuff is!), and became a pro at building financial models in Excel. I felt lucky to be surrounded by smart and highly motivated people, most of whom were quite nice.?

At 23, I had access to CEOs and CFOs of Fortune 500 companies, and while I did my fair share of book-binding and coffee runs, I learned a lot from my interactions with these intelligent and accomplished executives. I learned that even in the same role, different executives could have widely different approaches. I gravitated towards the “operators,” specifically the ones who wanted to get into the details and knew their numbers cold. I found the Analyst role to be well-defined and a good fit for someone like me: able to function on little sleep, had a keen eye for formatting errors, and wouldn’t give up until all model errors were resolved. I was fortunate to experience the “heyday” of banking with lavish closing dinners and golf outings. And I admit the excess was fun. I remember flying from a deal-closing celebration in Vail, Colorado, directly to a golf outing in Scottsdale, Arizona, and thinking about how surreal my life seemed compared to my friends back home. But I also experienced the darker side - being asked to pick up a designer dress for a client’s mistress and being so exhausted from repeated all-nighters that I had to sneak a power nap in the stall of the ladies' room, resting my head on the roll of toilet paper.?

The problem brewing – besides the impending 2008 financial crisis, of course – was that I didn’t like my bosses’ jobs. Banking has a very clear career path, and this is comforting to folks who like to know the rules. But, if you don’t like where that path leads, there aren’t many alternatives. I didn’t think much about it at the time; I was enjoying my current role, and I was loyal. I decided to stay on for a third year at Lehman Brothers and go straight into the Associate program. After committing to the program, I had the opportunity to work from our Hong Kong office, and in 2007, a lot of deals were happening in Asia. So I packed my bags, ready for a new experience in China. The work was the same, but the environment was different. For the first time, I stuck out as “different.” I didn’t speak the language or look like I belonged. It was an adjustment initially, but I enjoyed my time in Hong Kong. I embraced being an expat, learning how to say “Mosque Street” in Cantonese and finding the most efficient route to work down the Mid-Levels escalator system. My time in Asia also sparked a passion for travel that continues to this day.?

In the summer of 2008, I came back to a country where things were very different from when I had left. Bear Stearns had collapsed, the financial markets were depressed, and layoffs at Lehman had been ongoing. After completing the Associate training program, it was recommended that I rejoin my former group, where folks knew me, instead of starting my rotation in a new group. A few days later, Lehman Brothers went bankrupt and was bought by Barclays. What I remember most about the fall of 2008 was the overarching sense of anxiety around the office. The days were dull – no deals were being done – and there was so much uncertainty. Without work, all you could do was focus on the unknowns and take long lunches. Would we have jobs tomorrow? Health insurance? Who would be laid off next? Banking was no longer fun (or lucrative).

As the layoffs continued, only a handful of junior folks remained. It seemed inevitable that my name would be called at some point, and I started to think about what I would do if that happened. I thought of going to another financial institution or into private equity, but if I could even find someone hiring, I still had lingering doubts about whether this was the right long-term career for me.

What did I want to do when I grew up? I had no idea. I needed time to figure it out. So, I decided to take the socially acceptable “break” known as going to business school!

I attended The Wharton School at the University of Pennsylvania and naively thought that I would experience something akin to divine intervention while sitting in one of my classes, suddenly realizing my destined career. This did not happen. I took classes in marketing, sports management, operations research, strategy, and international finance. I tried consulting for the summer, but nothing fit. On a whim, a classmate of mine, Davis Smith suggested I take an entrepreneurship class, where the main project was to write a business plan for a startup idea. He already had an idea, and I would be responsible for writing the financial section. I was still trying to figure out my interests, and while I didn’t think that was entrepreneurship, I signed up for the class anyway.?

On the first day, Professor Ethan Mollick asked the class how many people were interested in starting their own businesses at some point. Everyone’s hands went up except mine! He looked at me and smiled as if to say, “Challenge accepted.”

This article is the second part in a series in which I’ll share my career journey—from finance to entrepreneurship to DoorDash’s global VP and Head of Analytics today. Coming up in part three is the story of how I failed spectacularly as an entrepreneur. If you missed part one, you can find that here.?