Trained as a philosopher, Weinberger's work focuses on how technology — particularly the internet and machine learning — is changing our ideas, with books about the effect of machine learning’s complex models on business strategy and sense of meaning; order and organization in the digital age; the networking of knowledge; the Net's effect on core concepts of self and place; and the shifts in relationships between businesses and their markets.

[2] From 1986 until the early 2000s he wrote about technology, and became a marketing consultant and executive at several high-tech companies, including Interleaf and Open Text.

[3] His best-known book is 2000’s Cluetrain Manifesto (co-authored), a work noted for its early awareness of the Net as social medium.

[8] In 2008 he served as a visiting lecturer at Harvard Law School and co-taught a course on "The Web Difference" with John Palfrey.

Beginning in 2015, Weinberger turned much of his attention to the philosophical and ethical implications of machine learning, resulting in a series of articles, talks and workshops, and his 2019 book Everyday Chaos.