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.

As a debater, Sterling was half of a team that ranked quarterfinalist at the Yale Intervarsity, semifinalist at the United States Universities Debating Championship, and runner-up at the Pan Pacific, Pan American, and U.S. Western Regional Debating Championships.

As a slam poet, Sterling became Hawai‘i state champion at age nineteen. Most recently, he coached a team from Hawai‘i to a second place finish at the National Poetry Slam. His greatest accomplishment is making his mother proud.