John
Cowgill
Partner
Cybersecurity, Applied AI
Costanoa’s Guinea Pig Associate
Wayward Kentuckian
Theater School Dropout
Former Consultant
Dad
Willing to pick the right battles
Every investment I make starts with a founder whose conviction in what they are building is contagious.
John
Cowgill
Partner
Cybersecurity, Applied AI
Costanoa’s Guinea Pig Associate
Wayward Kentuckian
Theater School Dropout
Former Consultant
Dad
Willing to pick the right battles
Every investment I make starts with a founder whose conviction in what they are building is contagious.
My Philosophy:
The best part of venture is partnering with founders who see the world not as it is, but as it could be—and are hellbent on making it real. Supporting those kinds of people through the highs, lows, and hard calls is what makes this work so fulfilling.
Early-stage investing is ultimately all about people who have put it all on the line to pursue their dream. My role is to be a useful partner through it all: listening closely, challenging assumptions when it helps, and staying aligned through moments both obvious and ambiguous.
What I value most are founders who mix ambition with humility. People who are obsessed with their craft, learn fast when they’re wrong, and keep pushing when others would quit. Venture is a long game, full of messiness, reversals, and moments that test everyone’s patience. The privilege of this work is standing beside people in those moments, helping them make the hard calls, and watching them turn improbable ideas into enduring companies.
Experience:
I’ve been in venture since 2016, backing early-stage teams building AI-native applications and the infrastructure that powers and protects them. At Costanoa, I look for founders with a sharp point of view, deep customer insight, and the grit to keep going when things get weird. I invest behind people first: those with bold ideas, unshakable conviction, and the humility to grow fast and keep learning. Prior to Costanoa, I advised tech and consumer companies on strategy at McKinsey, and before that, worked in business development at Techweek, a national tech conference series. That gave me a front-row seat to startup energy, along with a mild case of tech-conference PTSD (an occupational hazard in this line of work).
A Little More About Me:
The current rotation of hobbies includes cycling, science fiction, 20th century history, and trying (with mixed results) to meditate. The constants are my wife, our two hilarious and high-energy boys (TJ and David), and a few well-loved guitars.
CURRENT INVESTMENT INTERESTS
Autonomous AppSec, Identity & Access 2.0, Shared AI Workspaces, Space Domain Awareness