You mention an early entrance into the startup world. Can you tell us about that?
After my sophomore year in college, I had a summer internship opportunity. I was working at a startup for a two-month long program. Well, it was supposed to be two months long, but a month in, the company ran out of money, as most startups do. It was amidst the financial crisis of 2008.
I had two choices: go back to school or join the team and help pivot the business. I had nothing to lose; I could always go back to school and there were only four other guys working on it at the time. I ended up staying along and joined full-time. In the Summer of 2008, we ended up launching what became Groupon.
How did you manage studying and working full-time once you joined Groupon?
I was at Indiana University at the time which is a four and a half hour drive from Chicago. Groupon was in Chicago so I had to transfer. The one school accepting transfer students at the time, around late August, was DePaul University.
I transferred and would attend classes whenever I could. Mainly during late afternoons, evenings, and over summers. I had a lighter load because I was working full time. It took a lot longer, but I was able to finish.
What about that experience made you gravitate to the startup world thereafter?
I always loved working from a young age. School was something I knew I should do, but I always saw it as a place to learn how to learn. Rather than focusing on the topics, I was trying to learn the best practices for life.
I had been studying Finance and Economics to become an investment banker, like my father and older brother. After joining Groupon, I realized I could never go back to putting together financial models at an investment banking firm.
What was your official, and perhaps unofficial, role at Groupon?
When I joined, I became the Head of Global Operations. At a startup, that’s just a title. You end up holding a variety of responsibilities. My four cofounders had engineering backgrounds so that was what they worked on. My role was to do everything else that needed to get done. That included operations, but also finance, accounting, sales, and marketing. In a new startup, you wear all the hats that you need to.
As the business grew, I settled into operations. When we went on a massive M&A path, I was focused heavily on expansion and acquisition. That included acquiring competitors and potential businesses to integrate. I handled the operational integrations, partnerships, and strategy there. That was my role then on until our IPO in three years, which was very accelerated for our business.