Prior to RedOwl, Guy co-founded Berico Technologies, a high-end engineering firm that services the federal government, and launched Oxpoint Holdings, an investment arm that has invested in and incubated multiple private ventures. He began his career as a US Army intelligence officer, serving in Korea, Italy, Germany, and Afghanistan, and finishing his service at NSA. In 2007, Guy received the National Intelligence Medallion, the nation's highest award for non-governmental personnel, for his efforts in Iraq as the analytic lead of NSA's RT-RG program.

He was born in Cleveland, Ohio, holds a B.S. in Economics from the United States Military Academy (USMA) at West Point, and received his B.A. and M.A. in Philosophy, Politics, and Economics from Oxford University, where he studied as a Marshall Scholar. He is Chairman of the Commit Foundation, a non-profit that aims to enable serendipity for transitioning veterans through intimate mentoring workshops and one-on-one transition assistance.