Sterling is often wrong, but always seeks truth. He was raised in Nu‘uanu. After graduating from Roosevelt High School, he attended Honolulu Community College and the University of Hawai‘i at Mānoa. Then, he earned a master's degree in education from Harvard University.

Sterling now works as a debate coach and lecturer in the Department of Communication at Hawai‘i Pacific University. He also writes a column for Honolulu Civil Beat. At night, he is finishing a Ph.D. in education at the University of Hawai‘i at Mānoa.