Venkatesh Rao is a fun writer, but I wouldn't take his ideas very seriously. He tends to rely on broad associations, and tells "grand stories" using fuzzy categories, without a lot (or usually any) statistics to back up his rather broad and extraordinary claims. He also tends to name-drop famous philosophers, representing their ideas in ways one might generously call "heterodox".

In other words, he seems like a well-read and verbally intelligent "narrative-builder" like Freud or Marx, and about as accurate.