Interview #6 — Jessica Li
Driven, Creative, Family-oriented
are three adjectives Jessica Li, partner at Rough Draft Ventures and senior at Harvard uses to describe herself. I had the opportunity to have a conversation with Jessica:
You’ve obviously been involved in a wide array of experiences and have achieved some incredible things — tell me about where your motivation and work ethic comes from.
I think it’s a multitude of factors, but a lot of it stems from my dad. My dad was born in China and grew up homeless, and later on in his life he went on to become a professor in China by the age of 21. Since then, he has received 2 PhDs and now holds several hundred patents.
From him, I learned lots of things, but at the core there were really two lessons that stood out:
- Hard work — seeing someone create a lot from nothing while being super selfless, driven, and caring has been an incredible example for me growing up
- Thinking deeply about problems — I remember when he was teaching me math when I was in elementary school, he wanted to think beyond the answers and really understand “why?” there’s a particular pattern/result, and how I could generalize it.
I think both of these lessons have shaped how I approach problems and played a significant role in my drive and motivation.
Given that you’re a triple major studying economics, mathematics, and computer science, given his combination I’m curious where you passion from venture capital stems from?
Obviously there’s a lot of good things about Harvard, but at the same time I also felt that this school is an echo chamber at times. When I see incoming freshmen, they’re usually from incredibly diverse backgrounds and geographies, but over time, I see these students become super homogeneous. While this is natural, at the same time there’s so much herd mentality and people make very critical decisions based on their peers.
That being said, I found the entrepreneurial scene set itself apart from the rest of campus in terms coming up new and creative ideas for adding value to others. That being said, I noticed that student founders don’t have as much experience on the business side, and that’s where the entire venture ecosystems comes into play in terms of taking founders to the next level, and that’s where my passion stems from.
I know one thing you’re passionate about is the empowerment of women (evidenced through your involvement at Elpha and the Founder’s conference), especially in the context of venture capital. I personally theorize that a lot of this under representation can be rooted in women not going into STEM, as a STEM is a strong pipeline into many positions of influence like venture capital. What would you say to this hypothesis?
So I’d definitely say that the STEM barrier is one reason, but the way I see the mechanism working out is that there’s sort of “failed simulation effect” within venture.
I heard this quote, and I know it’s a generalization, but it basically assets that women are more likely to pitch traditional businesses whereas men are more likely to pitch unicorns, especially at the early stage. Moreover, I think women are more likely to focus on the details and the nitty gritty, whereas men are more open to talking about big, conceptual ideas. This leads to differences in how women pitch versus how men pitch, and often, the consequence is investors failing to the vision in women led ventures.
Furthermore, because of the hurdles in the STEM pipeline I think women are more likely start D2C ventures as opposed other types companies (like B2B for example). And then when you get to the investing stage, I think VCs find it easier to understand B2B business model more, and see a greater value in customer lifetime value, clients, ecosystem etc. On the other hand when it comes to D2C, a lot of VCs have the initial thought of, “would I use this product?”, and make a crude judgement based on that initial impression.
Adding on that, given that the vast majority of VCs are men it may be harder for them to empathize, although Glossier may be an exception.
You are a partner at Rough Draft Ventures. In past, I’ve traditionally asked interviewees what their biggest accomplishment was, but I want to ask the opposite for you. What would you say your biggest misstep or challenge was during your time at Rough Draft Ventures?
I started with Rough Draft in the fall, and while I had conducted informational interviews with folks in the space, I never really had hands on exposure doing due diligence with startups.
I remember my very first venture meeting — I was super nervous and had all these questions prepared and typed up. As a result, the meeting didn’t go as well as I’d liked because I was too rigid in how I approached the questions. I came in with a mindset that was too academic in nature, and set out to check a list of boxes rather than being adaptable and having a genuine conversation to understand what the startup was working on.
I think another thing I learned was how to pitch your own value add as a venture investor to the entrepreneur, because as a VC you’re looking to add value beyond just the money. That being said, I learned to tailor my conversations and add that personal touch and guidance while simultaneously evaluating the companies.
Post graduation, you’ll be working in investment banking at Morgan Stanley. How does this align with your interests, and what’s your roadmap going forward?
So I actually interned with the tech banking group at Morgan Stanley prior to accepting full time. So obviously there are a lot of downsides to banking, in terms of long hours and the work being tedious, but what I ultimately found a lot of parallels to venture where you’re helping these companies that are building large and impactful products spearhead their next chapter of growth.
Furthermore the team out in Menlo Park seemed to operate more as a tech company rather than a traditional investment bank, housed in a two story building rather than a skyscraper out in Times Square. I felt that it was much more reflective of tech and startup culture because we were very entrepreneurial and sought to find new ways to add value to clients while having limited hierarchy surrounding the entire pursuit.
I also think this opportunity gives me a birds eye view on everything going on and serves a strong launching pad, while also allowing me to build strong connections with firms in venture. In the medium term, I do want to work at a startup in the early stage so that I can get that operating and entrepreneurial experience under my belt, but also because I want to feel like the work I’m doing will have a long term impact — which contrasts to banking where your work can often feel very transactional.
Ideally, I’d like to get to a point where all my decisions are impact oriented rather than for financial motivations.
