Harvard in Tech Spotlight: Lily Sassoon, Partner at Green Meadow Ventures
I spoke with Lily Sassoon, Partner at Green Meadow Ventures, a firm co-founded by the Co-Founders and Co-CEOs of FabFitFun. Green Meadow invests in early stage consumer and enterprise software companies.
After graduating from Harvard College, Lily worked at Time Inc. doing strategy and M&A. Following a couple of years completing acquisitions of innovative media companies and analyzing startups and new business ideas, she moved to the tech world. She worked at Uber where she grew the New Jersey market and helped pass statewide regulations. After her experience at Uber, she attended Harvard Business School. While at HBS, Lily worked on her own startup in the frozen food space and also invested in student-led companies through Rough Draft Ventures. Post HBS, Lily led a team at Zola that launched a new vendor marketplace product for the company. She’s now investing in early stage companies in her new role at Green Meadow.
What is your favorite & least favorite part of being an investor?
I’m lucky that my role is never isolating or dull. Even while in quarantine and working remotely, I’m constantly meeting interesting, bold, and creative entrepreneurs tackling big problems, many of which have become even more overt and pressing because of the coronavirus. My generalist approach always brings new perspectives and challenges, as I learn the intricacies of markets I had previously never even heard of or discuss a controversial take on an industry that I had assumed I understood completely. Investing often requires me to suspend disbelief and open my eyes to new possibilities and ways of doing things. It’s always exciting when you meet founders and hear about ideas that inspire you to do so.
The hardest part for me is often feeling like there is never enough time. There’s always a tradeoff between meeting more founders and learning about new companies versus diving deeply and intensely into a smaller number of ideas. I try to balance casting a wide net with honing in on a few key themes. Oftentimes, speaking to many entrepreneurs, investors, and leaders actually brings clarity to a few particular concepts or theses.
What is the most surprising thing you have learned since starting VC?
It never ceases to amaze me how many individuals take the leap to start a company every single day. It’s a constant reminder that products and services can always be improved and that existing companies should never rest on their laurels or stop innovating.
How did your prior experiences prepare you for the VC role?
My background is in both operating and investing, so I’ve had the opportunity to sit on both sides of the table. My first job out of college was in strategy and M&A at Time Inc. I did my first Series A deal there and several acquisitions. In addition to honing my ability to analyze companies, I developed an understanding of how a strategic player thinks about expansion and growth via M&A. I still leverage this mindset when I’m evaluating potential exit options for investments. On the operations side, I grew the nascent New Jersey market at Uber, launched a new marketplace product at Zola, and experimented with founding my own company in the food space. These experiences give me a lens into the unique obstacles and opportunities that founders in particular industries may face and the general ones that transcend market and product. I have been in founders’ and operators’ shoes, which helps me ask the right questions and hopefully offer helpful feedback.
How did Harvard impact your work in VC?
In undergrad, I majored in History and Literature. I constantly read and analyzed texts and was pushed to articulate and defend my opinions both verbally and in writing. This opened my mind to new ideas and taught me how to consolidate various concepts and evidence into a coherent point of view that was firm, but that invited debate and adapted to others’ thoughts. This has served me well in VC, where my job is to absorb a lot of information on a variety of subjects. I have to form opinions quickly, often with many outstanding uncertainties. At HBS, the method of teaching was very different from that of undergrad, with case studies discussed among 90 peers who guide the takeaways and learning. With each case, we had access to a limited set of information, and had to ask the right questions, listen, and come to a data and fact driven conclusion by analyzing the case from several perspectives and angles. I try to take this collaborative and analytical approach to my job every day. And in both college and business school, my classmates were the best part! On top of the special personal relationships I built, I developed strong professional networks. My classmates have helped shape how I think and approach problems, and they’re still usually my first calls to discuss a new idea or brainstorm solutions to problems.
What is the tech trend you are most excited about moving forward?
There are two particular areas I’m really excited about right now. The first is the future of personalized health and wellness. Technology has already enabled consumers to take the first steps towards understanding and improving their health and wellness in a flexible and convenient way. The Apple watch, other tracking devices, and apps like Strava provide insight into physical activity levels and overall performance. Companies like Headspace and Peloton empower individuals to take care of themselves on their own schedules and terms. Over time, tech will not only facilitate the tracking of personal data and the virtual access to one-size-fits-all services, but will also, more importantly, gather individual health data and leverage the information to make key health and lifestyle recommendations and track progress. Parsley Health and others have begun this process by offering health coaching and robust, personalized medical attention at lower rates than have been historically available. Technology will further lower costs, more efficiently and cheaply collect and analyze health information, and create innovative methods to produce, deliver, and update recommendations. This will mean faster, cheaper, and more effective care for a wider audience. I really enjoy talking to founders working on companies in this space.
I’m also really excited about B2B tools that enable the consumer economy. Consumer companies rely on a variety of services and software to get off the ground, grow, and thrive. Shopify, Slack, and Stripe are great examples of the businesses that compose the infrastructure and foundation of many startups and established companies. In this new, mostly virtual world, I’m interested to see what the next generation of platform, productivity, and collaboration tools become and how they build and improve upon the existing ecosystem. As someone who has worked at several startups, I understand the critical need for these tools and how they can best be put into practice within companies. I love chatting with startups in this space.
How do you keep learning on/outside of the job?
I’m known in my family as the one who asks a lot of questions, and that is true in both my personal and professional lives. I have found that asking questions builds deep personal relationships. It also often helps uncover interesting and provoking ideas and pushes people’s thinking.
How do you stay in touch with the Harvard network?
Definitely through Harvard in Tech! After college I served on the board and helped bring Harvard alum founders (Jenny Fleiss, David Haber, Davin Chew, and others!) to the community to share helpful tips and lessons from their experiences as entrepreneurs. The series was intimate and created connections among Harvard alums across years and industries. In general, the organization provides really high quality content and creates a strong sense of connection. While at HBS, I was a partner at Rough Draft Ventures, General Catalyst’s student VC arm, and deeply enmeshed in the Harvard entrepreneurial ecosystem. I still maintain that close relationship. In general, my closest friendships were fostered at Harvard and HBS, and they remain my strongest and most meaningful. So my personal relationships tie me to the school in a really special way.
