Hiwatashi began skating at the age of five after a rink opened near his house. He competed on the juvenile level during the 2008–2009 season, placing fourth at the Upper Great Lakes Regional Championships. Continuing as a juvenile in 2009–2010, he won the bronze medal at the Upper Great Lakes Regionals before finishing sixth at the 2010 U.S. Championships. During the 2010–2011 season, he won the juvenile gold medal at both the Upper Great Lakes Regionals and the 2011 U.S. Championships.