Interview with Chris Offensend ’10

Chris Offensend graduated UVM in 2010 with a degree in mechanical engineering. He went on to pursue graduate studies in aerospace engineering at Georgia Tech before launching his career at Boeing. Throughout these experiences, Chris paid attention to what he wanted. And that desire led him to business school and entrepreneurship. In this interview, Chris talks about his journey and the early indications he felt leading him to start his own business. He offers students a helpful framework for how to approach their internships, as well as the different stages of their career, thinking of each experience as an experiment to test a hypothesis.

Sam: Chris, could you tell me about your story and how your path set you up for a successful start-up?

Chris: My story is a winding one. I started out at as a mechanical engineer major at UVM. But even by my junior and senior year, I still lacked a clear sense of where I wanted to go. My classes were good, and I really enjoyed the advanced courses. That uncertainty led me to go to graduate school.

Graduate school helped me in a couple of ways. It involved a lot of system design, which would serve me later. It also helped me to land an internship in aerospace that led to my job at Boeing.

My work at Boeing put me in a context that I was not used to; I was involved in manufacturing, research, and development – subjects that my UVM courses only provided a generic understanding. But it did involve a great deal of problem solving, which I enjoyed.

I encountered a personal problem when the Boeing corporation made the decision to move away from Seattle. I was not willing to relocate. This challenge led me to think more broadly. As a result, I enrolled in a Startup Weekend program, where participants would quickly move from ideating, pitching, and then launching a project all in the course of a weekend. It led to a lot of failure, but the experience was highly formative.

As a result, I became more curious about starting my own venture and decided to enroll in business school. As I learned about business theory, I wondered about if I still had what it takes to launch a start up. When it came time to secure an internship, I ran the experiment by joining an early-generation startup. I learned a lot, but the whole time I was asking myself, ‘is this a fit for me?’ The whole internship experience was transformative. It taught me a lot about scale, and I was empowered after that to go back and revisit my vision.

Sam: What immediate experiences led you to the idea for your startup?

Chris: There are people who are shoe-horned into entrepreneurship. These are the people who solve a problem, whose idea itself holds tremendous value. The process then becomes a matter of commercializing that existing idea. For people like this, entrepreneurship is kind of forced on them. 

And then there are people like myself, who op in to become entrepreneurs. The reasons can be different, and for me it was a desire to be impactful, to address social concerns through a double bottom line. When entrepreneurship is your decision, then you have to decide what is the problem area that you want to tackle. The key is to find a problem that holds enough energy for you that it can sustain your efforts for five to ten years. 

I found that problem area with a former UVM roommate who was telling me about the problems local governments face in procurement. The problem is costly since it involves steep overhead that can overtax local municipalities. And through our startup, Qwally, we are able to help local governments address that procurement issue.

Sam: What is some advice that you would give to students who are now studying at UVM and may have entrepreneurship aspirations? 

Chris: I think internships are a big one. For me, this was a transformative experience. Every internship is like a career experiment. You get to run a test on a career hypothesis. Even if the internship is a bad fit, you can ask, why was this a bad experience? What went wrong? What did I learn – not just about an industry, but about yourself?

I remember one internship I had at UVM. It was not a good fit for me. It did not match my expectations. But I learned from that experience by asking myself: do I like this? Do I want to do this? The reaction is either hot or cold. In that case, it was cold, and I moved forward.

Sam: You had a couple of experiences in graduate school. Could you talk about the differences in those settings and how they shaped your journey?

Chris: It is important to understand that in graduate school you can’t always get what you want, but you do need to know what you are looking for. In my first setting, I gained a lot of exposure to a subject area that was a good fit. I even thought about a PhD for a minute; but that was another experiment that didn’t play out. The experiment as a whole did play out, though, because it increased my overall career options.

From there, I continued to follow my gut. This was certainly true by the time I went to business school. From the first setting to the second, I moved from a focus on one particular industry to a general, or broad range of possibilities. This range offered me more flexibility; it opened more options. It allowed me to diverge from my current trajectory. In business school, everyone was doing something totally different; and I suddenly became aware of options that I had never considered. It was really inspiring. Again, this allowed me to run lots of career experiments, helping me to refine what I wanted to do, so that I graduated feeling much more confident about where I wanted to go.

Sam: I can tell this was transformative. Could you tell me more about what you felt in that space?

Chris: It was definitely overwhelming at first, but then it was inspiring. I go back to the startup weekends. That experience was completely overwhelming. I left that not exactly feeling confident, but I knew I needed more experience. I think experiences of overwhelm can teach us about those gaps in knowledge or skills. It is an opportunity for us to develop ourselves. The startup weekends gave me a basic framework to work on those gaps, when I got to business school, it clicked and everything suddenly made sense. 

As an entrepreneur, you are going to experience overwhelm. There is always a gap between theory and practice. And the bridge between those two is curiosity. Entrepreneurs have to be inherently curious to succeed. It is my biggest driving force. That curiosity pushes me to keep seeking out new experiences. If I encounter something new, I can join in, learn from it, and test more hypotheses. It doesn’t hurt to have a good fall back. In business school, I thought, I can always pivot and take on a job. I knew lots of classmates whose experiments failed, and they took a job somewhere. But in either case, the day to day is the same: positioning yourself in a new place where you can learn and operate to position yourself for the next experiment. 

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