Matt Cheng's investing style grows directly out of his years as a competitive tennis player, where he learned to read people, solve problems alone under pressure, and make fast decisions—skills he now uses to judge founders quickly, often writing a check after just one meeting, and to focus more on how a founder thinks and handles their own weaknesses than on the specific idea they pitch. This same unconventional path shows up throughout his life: he skipped the usual sports-recommendation route into National Taiwan University and finished his degree in three years, backed Calm's founders early because he saw their genuine passion for meditation, and has built his career across Taipei, the U.S., Greater China, and Tokyo while crediting his success mainly to a positive, resilient attitude and a lasting belief in himself.