Rick Grinnell

Rick Grinnell is a Founder & Managing Partner of Glasswing Ventures, where he invests in AI-native security and enterprise infrastructure startups. With more than 25 years as a venture capitalist and operator, he has backed and scaled some of the most dynamic companies in security and enterprise tech. Rick currently serves on the boards of Allure Security, Black Kite, Cydelphi, Nametag, Realm Security, Sigma Automate, and Trustle. His prior investments include multiple successful exits: Digital Guardian (HelpSystems), EqualLogic (Dell), Prelert (Elastic), Resilient Systems (IBM), TrackVia (Primus Capital), and VeloBit (Western Digital). Beyond investing, Rick is deeply engaged in the Boston innovation ecosystem. He is a Board Member of MIT Sandbox and the Advanced Cyber Security Center, serves on MIT’s Educational Council, and advises at both Harvard Business School’s Rock Center and MIT iHQ.