071: Rick Grinnell of Glasswing Ventures

Boston Speaks Up

Guest Rick Grinnell is the Founder and Managing Partner of Glasswing Ventures, a venture capital firm that invests in pre-seed and seed-stage companies in AI and frontier software technologies. Grinnell is one of the most reputed cybersecurity investors in venture capital land. For the last 21 years, he’s been investing in the various evolutions of security, storage, and SaaS-based startups out of his home base in the Boston area. He’s become such a local staple in the Boston innovation ecosystem that if you’re in venture capital and ever make your way to Boston, it’s an absolute must that you meet him--not simply out of business reasons but out of the plain fact that he’s one of the most interesting, multifaceted characters you could ever meet in venture capital. Grinnell is someone who defies categorization. If you get to know him a little more, you’ll learn that he’s a phenom on the pipe organ and skilled at enough instruments to form a one-man band if he really wanted. Check out his LinkedIn page, and you’ll see not just the standard listing of past roles and accomplishments, but a bio populated with his current music playlist: Twenty One Pilots, Alan Walker, Michael Franti, Sharon Jones, and the Dap-Kings. In fact, it was his passion for music--specifically a fascination with the creation of digital sounds through electronics--that prompted him to study electrical engineering and computer science at MIT. While Grinnell is a venture capitalist by title and reputation nowadays, he very much remains the same essential spirit as before: a lover of great music, a self-described tech “nerd” and a gravitational center for those around him.