A graduate of Bowdoin College, he became the first visual artist to be granted a PhD from MIT (interdisciplinary studies in Psychology and Art, 1986).

In the early 1980s, Siler made an extensive study of genius across numerous disciplines to see what, if anything, such highly creative people as Albert Einstein and Sergei Rachmaninoff have, or more importantly do, in common.

He studied art as an undergraduate, spending a year "apprenticed" in the studio of American artist Leonard Baskin.

In his 20s Siler was part of the same SoHo art scene which launched Julian Schnabel, Francesco Clemente and David Salle.

with the Cherry Creek School District (Colorado) to pioneer experiential learning methodologies based on the understanding and creation of systems of metaphor.