How did you know you were ready?
I don’t think you ever know you’re 100% ready. It’s hard to ever truly know this about yourself. For us, we had a bit of a push when we realized that we couldn’t both be students and entrepreneurs at the same time. We had to decide, and in that situation we felt ready so we went for it. I think there are signs though. For me, I have always gravitated towards operations things. I was a consultant at McKinsey for 4 years after undergrad, but I was always very ops-driven and one of the last things I worked on there was a product line for a social media-related product, which is very different from typical McKinsey projects.
What are some things you’ve been surprised to learn so far?
I’m surprised how much of a tech company we’ve become, and what that’s meant for us as a business. We’ve found our niche as a tech-enabled service layer between users and other services. This new space is sometimes hard to communicate to users, despite the benefit to them. This has been an interesting dynamic I didn’t anticipate when launching Alfred.
Why should people pay attention to HBS alums in alley?
HBS in many ways was our incubator. The idea started and was developed on campus during my first year spring break, and our first office was in a Cambridge VC’s extra room. HBS really created the environment for us to chase this idea. We had a little bit of money, were around great people in a space to keep us disciplined. When we took a leave of absence, we were still in Cambridge working on Alfred. We had great support, but it was still an abnormal thing to do. I think that’s a big difference between HBS and other schools, entrepreneurship is still kind of “underground”, but because of that the people who get involved are great. I expect that same selection will apply for Alums in the Alley, so we should see great things.