Meet the VCs: Glasswing Ventures

*Applications close on Friday 19 June, @5pm

Glasswing Ventures is a first-capital-in venture firm based in Boston, investing in AI-first, frontier technology, and cybersecurity companies shaping the future of enterprise and security, and they want to talk with YOU.

This session is a small group dinner and discussion, not a formal talk or panel. Attendees will meet Glasswing investors who think deeply about where AI is actually going, and learn how they evaluate technical founders building in enterprise and security before the category is obvious.

What you'll take away:

• How Glasswing evaluates AI-native startups at the earliest stages

• What they look for in technical founders before there's a product or traction

• How to build a relationship with investors well before you're ready to raise

Glasswing invests at pre-seed and seed, works closely with founders pushing into new technical territory, and often meets companies long before a fundraise. This is a chance to ask questions you wouldn't ask in a public setting.

You do not need a startup or a pitch deck to attend. Curiosity and thoughtful questions are encouraged.

Selected participants will receive location details in advance.

Participating Glasswing Team Members

Rick Grinnell is Founder and Managing Partner of Glasswing Ventures, where he invests in AI-enabled security and enterprise infrastructure. With 24 years in venture capital, he has backed standout companies across security, SaaS, and analytics — including several acquired by Dell, IBM, Elastic, and Western Digital. Before Glasswing, he was Managing Director at Fairhaven Capital and held senior engineering and marketing roles at several tech companies. Rick is a Venture Capital Advisor at Harvard Business School's Rock Center for Entrepreneurship, a member of MIT's Educational Council, and a Board Member of the MIT Sandbox. He holds BS and MS degrees in Electrical Engineering from MIT and an MBA from HBS.

James Masaquoi is a Senior Investment Associate at Glasswing Ventures, where he focuses on AI-enabled security and enterprise infrastructure investments. Before Glasswing, he spent three years at Osage Venture Partners investing in early-stage B2B companies across vertical SaaS, cybersecurity, and supply chain. Earlier in his career, he managed $300M in accounts at Amazon and co-founded 360VR Technology, a software startup that raised over $300K and closed pilots with large enterprise clients. James holds a B.A. from the University of Delaware and is a University Innovation Fellow at the Stanford Hasso Plattner Institute of Design.

*A Note About the Series

Meet the VCs sessions are informal networking and educational opportunities. They are not confidential settings. We encourage attendees to use their judgment about what they share.

If you receive a term sheet, investment offer, or any formal agreement through a connection made at one of these events, the Grid is not a party to that process. We recommend consulting an i-lab legal advisor before signing anything. You can also seek guidance through the Harvard Law Entrepreneurship Project, the Harvard Grid Lab-2-Market Monthly Series, and email questions directly to us at grid@harvard.edu.