Randy Moss arrived in Alaska in 1970 and one of the first people he met was Iron Dog Hall of Famer Ray Debenham. Ray and Randy became good friends and explored Alaska on dirt bikes and snowmobiles as Ray embarked on one adventure after another. After traveling to every old mining town and abandoned cabin in the state, Ray asked Randy to join him in climbing Everest and then to float the Amazon. Randy had to tell him no but in 1995, Ray asked him to run the Iron Dog and this time Randy said yes.

From 1995 through 1999, Randy entered the Iron with Ray Debenham as his partner. During these years, he became aware that there was a serious need for a checker in Ruby. The longtime local volunteer had retired and the Iron Dog was having trouble finding a dedicated replacement. From 2000 through 2003, Randy and Ray manned the Ruby checkpoint, pumping gas and recording times.

In 2004, Galena had some issues so Ray Debenham went there with members of his family to man that checkpoint, leaving Randy as the sole checker in Ruby. Randy and Ray usually rode from Fairbanks to their respective checkpoints, traveling over 500 miles of often unbroken trail. Once in Ruby, Randy would spend the entire race sleeping in the 10 X 10 gas shack between racers arriving.

Randy enjoyed his time in Ruby so much that in the summer of 2004, he bought the old roadhouse there and built a log cabin for summer use.

Randy Moss has been a one-man checking and gas crew in Ruby since 2000 and continues to help the Iron Dog in any way he can. Without Randy Moss and others like him, the Iron Dog would not exist.