I'd always assumed that the photo was in fact of 90s acid jazz outfit Jamiroquai's lead singer Jay Kay, and was some kind of obscure personal in-joke.

Or that in fact Smillew was the fictional alter ego of Jay Kay himself, and that posting humorous and instructive articles on Medium was what he did to unwind when not saving the planet by driving his collection of overpowered supercars and leaving threatening messages on journalists' voicemail.