Constanoa

Why I’m Joining Costanoa: Backing Unconventional Founders with Equally Unconventional Support

Sep 10, 2025

Sean Cai, Associate

If you want to invest in unreasonably-driven and exceptional individuals, I believe you need to be an exceptional investor.  Top percentile talent often congregates, even if coasts and organizations apart, and I’ve always wanted to be an investor who tries to be the best founder-partner and do it in the most unorthodox and effective ways.  That’s why I’ve joined Costanoa’s investment team.

At 16, someone took a bet on me and flew me out to a high school accelerator in the Bay, ultimately offering me a SAFE to build what became B2B EdTech SaaS for school districts. Selling to school districts while a student myself was difficult, but put me in the company of founders who did unreasonable things. I spent the next 6 years of my life learning everything I could about investing – as an EIR fellow at Canaan Ventures in college working on 360 video conferencing, and then as a venture fellow at General Catalyst & Hummingbird Ventures seeing what “great” looked like and where it came from.  Having gotten to work with both smaller operator-centric VCs and larger funds, I fell in love with building a venture firm that combined the merits of both.  I firmly believe that Costanoa is that place.  

The Costanoa team invests from first principles and providing their assistance to founders is their partners’ top priority.  They can act with the speed of smaller VCs, with the conviction and thoughtfulness of domain experts, and with the networked value-add of much bigger firms.  They combine the traits of all the best investors I’ve seen and I’m eager to work with founders under the Costanoa banner.

A mentor once told me investors were only good at giving money and helping with hiring. But I’ve always seen that as a starting point, not the ceiling. That’s why I’ve spent nights and weekends with startups I’ve backed doing everything from acting as an extra engineer building integrations and internal tooling, cold-calling enterprises to initiate GTM motions, and helping set up product metrics dashboards. Founders put their lives into their companies and deserve investors who hustle just as hard. The best investors go to bat for the founders they’ve backed  and are just as scrappy.

I feel lucky to be able to work with founders this way.  Exceptional, highly autonomous people who make the decision calculus to found a company are the most obsessive domain experts and help drive the world forward.

If you’re looking for an investor who’ll be just as scrappy as you, please reach out!