In 2013, Gregory was injured while hiking and bouldering. He had taken his dog for a walk, searching for the perfect bouldering spot. When he regained consciousness, he was in the ICU of the hospital where he worked, nearly two weeks later. The spinal cord injury resulted in the loss of sensation and movement in his legs. Despite this, Gregory has adapted his passion for the outdoors. He continues to enjoy activities like surfing and fly fishing, spending quality time with his friends and family.