How we design and structure our information in the Web is essentially influenced by our philosophical viewpoints on what the Web is. In this paper, we compared two fundamentally different positions: one takes the Web to be a web of documents and the other a web of things. By using Fred Dretske’s semantic information theory, we discussed why we should favor the second model over the former through our formulation of two information triads. The first one is the Knowledge-Information-Data (KID) triad that allows us to clearly define these concepts within a communicative praxis. The second one is the Symbol-Information-Referent (SIR) triad that allows us to clearly define and connect all kinds of information systems, regardless they are the man-made or naturally occurring ones.