April 10, 2024 | Firm News

Becoming a VC: It’s Not What You Think–and Neither Am I

Rebecca Li

Written by

Rebecca Li

I still vividly remember the first time I visited San Francisco in 2012. I spent the week hanging out with my friends’ community of startup founders and felt that a whole new world opened to me. The vibrancy of the community, the dare to dream big, and the electric atmosphere of creative ideas cross-pollinating left me mesmerized. At the end of the trip, I remember standing at the Golden Gate bridge vista point, overlooking the bustling city of San Francisco at the edge of the Pacific West Coast – symbolizing the frontier of humanity and technological innovation. Since that moment, a question began to take root within me: Who am I? Is there a role for me in the project of exploring human frontiers that this place has taken on?

Venture Capital was not the immediate answer. After doing consulting at General Electric for 6 years, I deeply appreciated the breadth of knowledge I gained, yet I knew I wanted something deeper. A place where I could stay for a long time and see through the ups and downs. A small group of people with big ideas who are “optimistically delusional” enough to believe they can make a difference.

With that longing, I joined a 300-people startup called Databricks, leading its go-to-market strategy. I got everything I was hoping for, especially a team of wicked smart technical founders trying to build a business with awesome technology. And it was really really hard. 

We were rapidly iterating on all fronts simultaneously – the backend technology, the UX, the price & packaging, the market segment, and the sales motion. It felt like re-building every single part of an aircraft while it was flying. And that call for strategic thinking and precision of execution accelerated the growth of all the founders and myself. I loved the intensity and felt a strong sense of fulfillment being the enabling factor at the startup. And when it got big, I knew I wanted to do it again. 

Searching for the smartest technical founders, I quickly found myself in the machine learning world of people solving autonomous driving and drug discovery problems. Weights & Biases, the well-loved AI developer tooling company, was at the intersection of these innovations and a no-brainer for me to join. 

Leading product strategy, I worked with the founders pivoting from an ML Engineer tool to serving a much broader group of Software Engineers in the GenAI era. It was hard, frustrating, nerve-wracking, exciting, fun, and everything in between. We made numerous design choices getting to the right balance between opinionated workflows and configurability; We did hundreds of customer calls and continued iterating on the right levels of product abstraction for different user persona; We designed a more flexible GTM/pricing strategy paired with a fast evolving market & product. … I found myself deeply drawn to problems that are not fully defined and to founders who have the stamina and ambition where just a little help gets them through the growth pain. 

It became more and more clear that early-stage VC could be a great fit for me. I get to work with smart founders and help them think through some of the biggest challenges as a startup – What is the biggest leverage point in the product given its use cases? How to land customers with a product wedge and expand into adjacencies? What is the best GTM strategy tailored to the market, the persona, and the product? And most importantly, how to piece all these components together at what sequential order so the startup engine can run smoothly with longevity? … And as a VC, I can do it for multiple companies at the same time! 

With all that excitement, there was this lurking fear: what “product” am I selling? At the surface-level, I am selling the most undifferentiated commodity – money. But, is that it? Or am I able to build partnership even from the outside and accelerate the team in a concrete way?  And that same  existential question that took root in me 12 years ago came back: who would I be and what would my role in this community look like?

Tony, a long-time friend and Partner at Costanoa, called at the perfect time. He is not a typical VC Partner you’d imagine – introverted, a deep thinker, no beating around the bush, no sales vibe, and despite all this, he’s  successful in venture. What makes him different is precisely what really smart founders love about him, and he loves his job. When Tony asked: “Do you want a trial with us to see whether you like it?” My eyes lit up. 

Following that was an intensive 2-month “VC school“ by doing the full job: sourcing, due diligence, and portfolio company help. I felt energized by every part of it: the autonomy, the different dynamics on each deal, the unique skillset investors gained by helping founders in every conceivable way. It showed me the core of the job: find great founders, enable them, work really hard with them, and repeat. 

The idea hit me – it is selling “Founder Enablement as a Service!”

The team at Costanoa has shown me a particular approach to Venture that resonates deeply with me. In many respects, it feels like a very natural next step for my own growth. I get to focus on finding founders who want and can be accelerated with my help, and be upfront with my style, knowing it may not suit everybody.

With that, I am officially joining Costanoa on the investment team as a Principal. I am very excited to be a part of bringing more Founder Enablement as a Service to the community.


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