Henry was born on January 9, 1885, in Neu, a little village in Tottori Prefecture, western Japan. In 1904, at the age of nineteen, he sailed to San Francisco, where there was a growing community of Japanese immigrants, many of whom were shosei (young student-workers).

Kiyama was a talented artist, and while working at a variety of jobs he attended the San Francisco Art Institute. He excelled at life-drawing and painting, and between 1915 and 1920 won several awards and mentions. He also won a scholarship from the New York Art Students League and exhibited his work several times in San Francisco. An April 20, 1920, article in the San Francisco Bulletin reported on an exhibit at the Palace of Fine Arts, and described Kiyama's work as follows: "[His no. 115], Old Wagon Shed, is a solidly modeled, well balanced and vigorously colored design, and his 114, Old House at North Beach, in room 15, in soft green and gray, is quietly effective."