Jennifer Carolan, co-founder and general partner at Reach Newschools Capital, is also a former managing partner at NewSchools Venture Fund.
VAULT: Can you tell us a little about yourself? What made you want to enter this career?
CAROLAN: Growing up in Chicago, I didn’t know about venture capital. I only learned about it in graduate school at Stanford University when I heard Kim Smith, the founder of NewSchools Venture Fund, speak. She talked about hybrid entrepreneurial teams and the importance of bringing educators together with entrepreneurs. My background is teaching; I was a middle school history teacher and became very interested in using technology and how it might be applied to differentiated learning. Going into venture capital was a slow evolution for me, from teacher, to venture philanthropy, to impact investor.
VAULT: Tell us a little about Reach Newschools Capital. What are some of the rewards and challenges of launching a VC fund?
CAROLAN: Reach Capital is an early stage impact investment fund focused on improving educational opportunity through seeding mission-oriented edtech entrepreneurs. We look for places where technology can make a unique difference. Most of our investments are in K-12 and amplify the impact of great teachers.
The best thing about this job is working with amazing entrepreneurs who want to have a positive impact on the world. They are the most hard-working, optimistic, and inspirational people I know (alongside teachers, of course). This is a service-oriented job and the entrepreneurs are our customers.
The challenge is you are spread across many investments so it can be difficult to prioritize and know how best to spend your time. I sometimes find it hard to give relationships the attention I would like in such a fast-moving and transactional environment. Two of my mentors, John Doerr and Brook Byers, are especially good at this and I have learned a lot watching them work with entrepreneurs.
VAULT: What are the most important personal and professional qualities for venture capitalists?
CAROLAN: They need to be comfortable being spread across different ideas, people, and types of work. They should be comfortable context-switching many, many times a day. For people who like to focus on one thing per day, this is not a good job for you. They should be willing to serve in a supportive role—we are behind the scenes, not out in front like the entrepreneurs. I also believe strong venture capitalists connect the dots well and see trends coming.
VAULT: What advice would you give to job seekers (especially women) in terms of breaking into the VC industry?
CAROLAN: Some believe it is important to have operating experience and that may be so; my operating experience was teaching, I guess. There are very few women in venture capital. I would recommend finding mentors in venture capital. Sheryl Sandberg’s chapter on mentors in Lean In has the best advice I’ve seen on the topic. I was lucky to learn from board members, bosses, and colleagues at NewSchools Venture Fund.
VAULT: What has been one (or more) of the most-rewarding experiences during your career, and why?
CAROLAN: The most rewarding experiences are believing in an entrepreneur when nobody else does, supporting them as they grow, and watching their ideas scale, reaching millions of people. In my case, I get to see their ideas impact millions of children and feel like I was some small part of that process. As a mom, another bonus is walking into my kids’ school, hearing their teacher rave about a science curriculum or a new tool that has revolutionized their teaching, and smiling to myself because our fund seeded it.
The above was adapted from the new Vault Career Guide to Venture Capital.
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