TWO SIDES, SAME COIN: How I left the Bay Area as an operator and returned as an investor
When I first told my team I was applying to business school, the immediate response I received was a bewildered “What! Why?”
“What! Why?” indeed. I was at a fast-growing tech company with an amazing culture, surrounded by smart, driven people that I enjoyed working with, and launching products that were making a meaningful impact on the future of work. The company was also having an unbelievable stock run. Leaving such an ideal situation at a post-acquisition startup seemed incredulous.
I love software and startups, and knew that I wanted to continue building a career in those spaces. Being immersed in Silicon Valley, I started to observe that entrepreneurship and financing were very much two sides of the same coin – who your capital providers were and the advice they gave could adversely affect a young company’s outcome, and similarly, backing the right founder could yield outsized returns for a professional investor. The countless examples of talented individuals ebbing and flowing into either role at different times (operator one day, investor the next) reinforced this insight. I knew that if I truly wanted to thrive in the land of startups, it was not enough for me to rely on my experience as an operator; I needed to understand the other side: the world of venture capital. With this aspiration, I left startup mecca for HBS to learn about term sheets and cap table mechanics.
While at HBS, I was able to leverage an incredible resource to help me learn more about venture capital: The Rock Venture Partners program. The program, run by Jeff Bussgang and the Rock Center (led by Jodi Gernon, Chuck Collins, and Priyanka Gandhi), is structured as a curated apprenticeship where a small group of EC students (RVPs) are responsible for a pool of funds and have to work together to invest in HBS startups and support these companies as they progress through the Rock Accelerator. As part of the program, Jeff also generously extends his time and network to help RVPs find internships and meet up with their VC role models. There are no pre-requisites, and all ECs (second year students) are welcome to apply. Here were some of the highlights:
Getting clarity on professional goals: At its core, this program is meant for students to get a taste of day-to-day VC life. Jeff always advised us to be introspective and we spend time at different junctures reflecting on our experience. In fact, after going through the program, many of my fellow RVPs realized this was not the career path for them, while others had their aspirations reinforced.
Growing on a personal level: There are very few times in life where someone hands you real money to invest in ideas you are excited about without concern for return thresholds! This was a low-stakes opportunity to learn and take risks, so I pushed myself outside of my comfort zone by partnering with non-software companies and investing in very early-stage ideas.
Partnering with entrepreneurs: Throughout the year, the RVPs select and work with HBS entrepreneurs entering the Rock Accelerator. While this was a low-risk exploratory program for the RVPs, many of the Accelerator applications were not simply pitch decks to evaluate; they represented my peers’ life passion and future career. It was imperative to keep this in mind whether I was supporting a founder as she was making a first hire or having a difficult feedback conversation with a team that did not receive funding. Having been an operator, I was already keenly aware that building a successful startup is extremely hard and emotionally taxing. The RVP experience gave me more insight into what it truly means to be a good partner to a founder, and I gained a newfound appreciation for the immense amount of respect, thought, and effort which forms the foundation of these relationships.
Collaborating as an investment committee: Each RVP batch gets full autonomy to design their own partnership structure and processes. As founding partners of our own “fund”, we had to learn how to collaborate effectively and work through any disagreement (e.g. on how to allocate funds or select teams). With the VC and startup community being such a tight-knit one, many of us will cross paths in the future so the trust and friendship built during the program have been phenomenal in fostering our working relationships.
Fast forward two years, while I find myself (quite literally) back in the same spot in my old San Francisco neighborhood, my views have evolved and progressed. This time the coin has flipped. I return equipped with more knowledge and passion for the startup industry, and also with more empathy for both founders and investors. The ability to understand both sides has shaped my investment style and philosophy, and I hope to bring this balanced perspective to Silicon Valley as I begin my next chapter here as a venture capitalist.
This post was originally published in Harvard Business School’s MBA voices blog.
Janelle Teng is from the Harvard Business School Class of 2020 and a proud member of Section C. From completing her undergraduate studies at Stanford University to working as a product manager at SalesforceIQ, Janelle has spent most of her academic and professional career in the Bay Area. While at HBS, Janelle was on the leadership team for the Venture Capital and Private Equity Club and the Women in Investing Club. She will be returning to San Francisco after graduation to join Bessemer Venture Partners as a growth-stage investor. She hopes that sharing her story will encourage everyone (regardless of background or prior experience) to make full use of the resources at HBS, such as the Rock Venture Partners Program and the Rock Accelerator, to explore and develop their interest in venture capital and entrepreneurship, as she would love to see more diverse voices in the industry and change the perception of what an “ideal VC” is.