Fleming grew up in Bloomfield, New Jersey and attended Bloomfield High School. He went on to attend Montclair State University where he studied Broadcasting. He is currently a court clerk for the Judiciary of New Jersey. In addition, he runs the Sports E-Cyclopedia and is a co-host on Chab Dog Radio on Sundays at 12 pm EST. In addition, he is a contributor to Barstool Sports.
Mets Opening Day 2017
On April 3rd, 2017, Fleming had tickets to attend the New York Mets Opening Day ceremonies. Leaving his home at 8 am, Fleming was on his way to the game when a train ahead of him was derailed. With the commuter service compromised, Fleming was forced to take an Uber to Hoboken, where he subsequently took the PATH into Manhattan and then transferred onto the 7 Subway Line.  Although Fleming was upset that he missed opening ceremonies, he was thankful to make it to the game and delighted with the result of a Mets win.
Fleming was interviewed by NBC 4 about his experiences commuting on NJ Transit to the Mets game. The broadcaster described Fleming's emotions as irate as he lambasted NJ Transit and their service. The video was picked up by Sports Illustrated and Barstool Sports and has since gone viral.