Insights from a Recovering VC and Current Operator

Post originally appeared in Breakwater Ventures Tide Charts.

My Approach

My core values as an early-stage investor mirror my core values as a person. I lead with curiosity and kindness, aim to give founders the freedom to build their companies, and focus on fostering community—to serve our founders and meet new ones.

Curiosity

I meet new companies with a beginner’s mind, focusing on asking thoughtful questions about them and their business. I strive to ask questions that reveal what a founder has learned and why they’re building what they’re building. Like any good salesperson, I listen more than I speak.

After a five-year hiatus from investing, during which I built companies as a founder and operator, I’m using my new experience to rebuild my investing mental models. Heuristics—mental shortcuts—are a valuable tool for early-stage investors, but with this beginner’s mindset, I’m working to move beyond pattern matching and instead evaluate each company through a structured framework.

Some of my old rules still apply, and I’m learning new ones.

Mainly, founders remain the most important factor for me. I focus less on industry expertise and more on their lived experience with the problem, a learning mindset, technical ability to solve the problem, and the capacity to sell a vision of the world as it could be.

I prioritize large markets. Right now, I focus on markets I understand. As Don Valentine famously said, “...don’t create markets; exploit markets early...with the right people.” In big markets with the right team, I expect competition, so I emphasize founder execution.

At the early stage, I focus on “hair-on-fire” problems for customers—problems so urgent that customers are willing to pay to solve them. If those conditions are met, the right go-to-market model usually follows.

I care less about the product itself at this stage and more about what the founders’ product decisions reveal—namely, their technical acumen, problem-solving ability, and the insights they’ve gained to get to this point. What have they learned along the way?

Kindness

Building companies is hard. I’ve never understood this more deeply than after building my own. Humility is essential—founders build businesses, not investors. As an investor, being aware of what I know and, more critically, what I don’t know, helps me build trust with founders.

I know I can help with go-to-market strategies for $0–1M. I can identify hair-on-fire problems, strategize MVPs, research markets, develop foundational business models, and advise on getting to $1M in sales. Beyond those areas, I stay quiet and listen.

Freedom

I want to give founders the freedom to make their own decisions. A personal goal of mine is to be the first call when a founder is working through an issue. Often, I simply listen and ask a few questions. I trust that the founders we invest in have what they need to make the next decisions. My role is to create space for them to arrive at their own solutions.

Community

I love building communities. Bringing people together creates opportunities for serendipity. I often focus on communities I’m part of, like Stanford and This Week in Fintech Angels, to meet new companies. One of my favorite pieces of feedback is: “I met [XYZ person] because of you, and now we’re working together!”

I enjoy organizing walks, hikes, and outdoor activities with friends and colleagues to help blend my communities. If you find yourself in the Bay Area in 2025, let me know!

Ultimately, investing is a people-first business, and it’s this philosophy that guides my approach to investing. Look forward to learning and growing alongside our community in 2025.