Upon his return to Japan, he enrolled in Keio University's Faculty of Policy Management, although he spent most of his junior and senior years backpacking in Asia and Europe.

[3] This book launched Kun's career as a freelance magazine writer[4] and editor for several major publications, covering a wide range of topics from subculture, fashion, architecture, film, music, photography, and art.

During this time, he interviewed over a hundred notable figures including Wes Anderson, Spike Jonze, Gus Van Sant, Jonathan Ive,[5] Marc Newson, Richard Hutten, Ken Kesey, Haruki Murakami, Raymond Pettibon, and Barry McGee.

It was around this time that Kun started producing music events with artists such as Kenji Takimi, The Avalanches, DJ Milo, 2 Many DJs, Yamantaka Eye of Boredoms, and James Murphy of LCD Soundsystem.

[6] Kun has made cameo appearances in several high profile films such as Sofia Coppola's Lost in Translation and Wes Anderson's movies The Grand Budapest Hotel and Isle of Dogs.