Rick Grinnell is the Founder and Managing Partner of Glasswing Ventures. See sector focus and contact routes.
Rick Grinnell is the Founder and Managing Partner of Glasswing Ventures, where he focuses on investing in AI-enabled security and enterprise infrastructure startups. His investment thesis targets pre-seed and seed-stage companies operating in AI and frontier software technologies, with a geographic focus on the Boston area and beyond. Grinnell has spent over 21 years investing in security, storage, and SaaS-based startups in the region, building a reputation as a staple in the local innovation scene. While specific check sizes and lead/follow behavior are not publicly detailed, he has backed and scaled dynamic companies in security and enterprise tech over more than 25 years as a venture capitalist and operator. Notable portfolio companies include Allure Security, Black Kite, Cydelphi, Nametag, Realm Security, Sigma Automate, and Trustle, with prior successful exits such as Digital Guardian, EqualLogic, and Prelert. Grinnell is also deeply engaged in the Boston ecosystem, serving on boards for MIT Sandbox and the Advanced Cyber Security Center, and advising at Harvard Business School’s Rock Center and MIT iHQ. He is an MIT and Harvard graduate, an avid musician
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