Gregory was born and raised in rural Illinois. While most of his childhood was typical of many children, Gregory did have a very positive experience with a counselor who helped him out during a difficult time in his life. It was then that he decided to dedicate his career to improving people's lives through the power of therapy. However, that was not his only area of interest.
During his last year of high school, Gregory had an idea for a book based on an older man discussing life with a younger man. The idea was tabled for many years as Gregory attended college and graduate school. Both of those experiences allowed Gregory to hone his writing abilities. He graduated from Augustana College with a B.A. in Psychology followed three years later by an M.Ed. from DePaul University. After school, Gregory continued to work on his story idea until a basic manuscript was formed and refined. The Man on the Bench was released nine years later in February of 2016, making it his first published book.
Additionally, Gregory found an interest in promoting knowledge and his passion for mental health in new and unique ways. Gregory has been involved in various podcasts during his professional career. Most recently, he hosts The GOBERT Report, a weekly talk show that explores the intersection of news, culture, and entertainment.
Gregory continues to serve clients, work on future manuscripts, and build his online academy Self Start Academy in Chicago.